Org. Synth. 2013, 90, 229-239
DOI: 10.15227/orgsyn.090.0229
Preparation of 3-Oxocyclohex-1-ene-1-carbonitrile
Submitted by Jesus Armando Lujan-Montelongo and Fraser F. Fleming.1
Checked by David Hughes
1. Procedure
A. 2-Bromo-2-cyclohexen-1-one. A 3-necked, 500-mL, round-bottomed flask, equipped with a magnetic stir bar (PTFE-coated, oval, 4 cm), is charged with cyclohex-2-enone (15.0 g, 156 mmol, 1.0 equiv) and CH2Cl2 (150 mL) (Note 1). The center neck is fitted with a 25-mL addition funnel equipped with a gas inlet adapter connected to a nitrogen line and gas bubbler. One outer neck is sealed with a glass stopper; the other neck is capped with a rubber septum through which a thermocouple probe is inserted (Note 2). The flask is immersed in a dry ice/acetonitrile bath and stirring is begun. After the internal temperature reaches -45 °C, HBr (48% aq. solution, 3.6 mL, 32 mmol, 0.2 equiv) is added dropwise via syringe through the septum in 1 min. The addition funnel is charged with neat Br2 (9.0 mL, 175 mmol, 1.1 equiv), which is then added dropwise until the orange-red color indicative of excess bromine persists (Note 3). After 10 min, the addition funnel is replaced by a clean 125-mL addition funnel charged with pyridine (25.5 mL, 316 mmol, 2.0 equiv), which is then added dropwise over 15 min (Note 4). After the addition, the cold bath is removed and the dropping funnel is replaced by a reflux condenser equipped with a gas inlet adapter, which is connected to a nitrogen line and gas bubbler. The mixture is allowed to warm to room temperature over 30 min, then heated to reflux (43 °C) for 1 h using a heating mantle. After cooling to room temperature the flask contents are transferred to a 1-L separatory funnel, the reaction flask is washed with CH2Cl2 (50 mL), and the additional solution is added to the separatory funnel. The mixture is washed with an aqueous solution of sodium thiosulfate (0.7 M, 150 mL). The organic phase is separated and the aqueous phase extracted with CH2Cl2 (50 mL). The combined organic layers are washed with 1M HCl (100 mL). The organic layer is removed and the acidic, aqueous phase is extracted with CH2Cl2 (50 mL). The combined organic fraction is washed with water (50 mL), brine (50 mL), and then filtered through a bed of Na2SO4 (50 g) into a tared 1-L round-bottomed flask. The solution is concentrated by rotary evaporation (40 °C, 200 mmHg) to about 60 mL (84 g), then hexanes (100 mL) are added and the concentration continued to dryness (Note 5). Vacuum drying (10 mmHg) to constant weight (1.5 h) affords crude 2-bromo-2-cyclohexenen-1-one (26.7 g, 98% yield) as a slightly yellow powder. The crude 2-bromo-2-cyclohexen-1-one is suitable for the cyanation-elimination reaction without purification (Notes 6, 7, 8).
Caution! Sodium cyanide and HCN are extremely toxic. The experimentalist should use sufficient personal protection and only handle sodium cyanide solid and solutions in a well-ventilated fume hood. The aqueous waste solutions containing cyanide should be treated with excess bleach before disposal.2 Good housekeeping is essential - all spills around balances or work areas should be immediately cleaned up and the area washed down with bleach.
B. 3-Oxocyclohex-1-enecarbonitrile. A 500-mL round-bottomed flask is charged with MeOH (120 mL) (Note 9), crude 2-bromo-2-cyclohexen-1-one (18.6 g, 106 mmol, 1.0 equiv), and a magnetic stir bar (PTFE-coated, oval, 3 cm). The flask is capped with a rubber septum and inserting an 18-gauge needle through the septum provides a nitrogen inlet. A thermocouple probe is also inserted through the septum (Note 2). The reaction flask is immersed in a tap-water bath and then neat AcOH (6.5 mL, 114 mmol, 1.1 equiv) is added dropwise to the stirred solution via syringe over 1 min. After 5 min, the septum is briefly removed, solid NaCN (5.68 g, 116 mmol, 1.1 equiv) is added in one portion, and the septum is replaced (Note 10). After 10 min a second portion of NaCN (2.73 g, 56 mol, 0.5 equiv) is added, followed, after another 10 min, by a third portion of NaCN (1.25 g, 26 mmol, 0.25 equiv), replacing the septum after each addition. After 20 min (Note 11), the water bath is replaced with an ice-water bath. Once the flask contents equilibrate to 5 °C, the septum is removed, and an aqueous solution of Na2CO3 (0.5 M, 100 mL) is added. After 1 min, solid NaCl (10 g) is added and the mixture is stirred for 5 min. The flask contents are transferred to a 1-L separatory funnel, the reaction flask is washed with EtOAc (100 mL), and the additional solution is added to the separatory funnel. The organic phase is separated and the aqueous phase is extracted with EtOAc (3 x 100 mL). The combined organic phase is washed with 5 °C aqueous NaOH (1M, 100 mL) (Note 12) and then washed with brine (2 x 50 mL). The organic phase is dried by filtering through a bed of Na2SO4 (50 g) into a tared 1-L round-bottomed flask. The solvent is removed by rotary evaporation (40 °C, 10 mmHg) to afford an orange oil (12.6 g), which is purified by column chromatography on Florisil (Notes 13 and 14) to afford 3-Oxocyclohex-1-enecarbonitrile (8.07 g, 63% yield) as a pale yellow oil spectrally identical to material previously reported (Note 15).3
2. Notes
1. The following reagents and solvents were used as received for Step A: Cyclohex-2-enone (Sigma-Aldrich, 95+%), HBr (48% aq., Sigma-Aldrich), CH2Cl2 (Fischer Certified ACS, stabilized), Br2 (Sigma-Aldrich, reagent grade), and pyridine (Sigma-Aldrich, ACS reagent, >99.0%).
2. The internal temperature was monitored using a J-Kem Gemini digital thermometer with a Teflon-coated T-Type thermocouple probe (12-inch length, 1/8 inch outer diameter, temp range -200 to +250 °C).
3. Bromine is extremely corrosive and an irritant and must be transferred within a well-ventilated fume hood. Dropwise addition of bromine at intervals of one drop every 2-3 sec, slowing to one drop every 5 sec near the end point, gave the best results. The entire addition time was 40 min. The internal temperature was maintained at -45 to -48 °C. An excess of three drops of bromine is typically added after the end point to ensure the orange-red color indicative of excess bromine persists. Unreacted starting material carries through to the next step and cannot be removed in the chromatographic purification of the nitrile product of step B.
4. Pyridine was added at a rate of about 1 drop/sec with the temperature rising to -39 °C. The reaction was monitored by 1H NMR by removing a 0.1 mL reaction aliquot and quenching into 0.5 mL EtOAc/0.5 mL 0.7M sodium thiosulfate solution, separating the organic layer, filtering through a cotton plug, and concentrating to dryness. Diagnostic 1H NMR resonances: starting material, δ: 6.01 (dt, J = 2.0, 10.3 Hz, 1 H) and 7.03 (dt, J = 4.3, 10.3, 1 H); product, δ: 7.42 (t, J = 4.5 Hz, 1 H).
5. The flush with hexanes results in crystallization during the concentration, which provides a product with greater stability. The solid obtained by concentration of the dichloromethane solution was found to be less stable.
6. The crude material was 95% pure based on GC analysis (tR = 9.7 min; conditions: Agilent DB35MS column; 30 m x 0.25 mm; initial temp 60 °C, ramp at 20 °C/min to 280 °C, hold 15 min). The submitters carried out a recrystallization of 18.0 g of 2-bromo-2-cyclohexen-1-one by dissolution in 25 mL of boiling EtOAc, filtration through a pre-wetted funnel with filter paper, followed by the addition of hot hexane (~4 mL) to induce turbidity, cooling, filtration on a Büchner funnel, and drying for 20 min at 0.01 mmHg, providing 13.3 g of white crystals (73% yield, mp 74-75 °C).4 The checker purified the product as follows. To a 100-mL round-bottomed flask equipped with a 2-cm oval PTFE-coated magnetic stir bar was added crude 2-bromo-2-cyclohexen-1-one (7.80 g) and t-BuOMe (10 mL). The slurry was stirred for 5 min. The flask was fitted with a 25-mL addition funnel through which was added n-heptane (10 mL) over a 10 min period. The slurry was stirred for 20 min at room temperature, then filtered and washed with n-heptane (10 mL) to afford 2-bromo-2-cyclohexen-1-one as an off-white solid (5.45 g, 70% recovery, mp 72-74 °C, >99% pure by GC).
7. 2-Bromo-2-cyclohexen-1-one has the following spectroscopic properties: 1H NMR pdf (400 MHz, CDCl3) δ: 2.04-2.10 (m, 2 H), 2.43-2.47 (m, 2 H), 2.60-2.64 (m, 2 H), 7.42 (t, J = 4.5 Hz, 1 H); 13C NMR pdf (100 MHz, CDCl3) δ: 22.8, 28.5, 38.5, 124.0, 151.3, 191.4; IR (neat): 3043, 1680, 1598 cm-1; HRMS (ESI) calculated for C6H7BrO 196.9572; found 196.9570 (M+Na)+; GC-MS m/z (rel intensity): 176 (M+, 78), 174 (M+, 77), 148 (87), 146 (88), 135 (24), 133 (24), 120 (38), 118 (38), 67 (100), 55 (42).
8. The checker found both crude and recrystallized 2-bromo-2-cyclohexen-1-one to be unstable at room temperature, decomposing within 3 days to a purple gum with release of gas. Material stored in the freezer darkened but remained unchanged by NMR for a period of 2 weeks.
9. The following reagents and solvents were used as received for Step B: methanol (Fisher Optima, 99.9%), HOAc (Fisher Certified ACS, 100.0%), NaCN (Sigma-Aldrich, ACS certified, 95+%), EtOAc (Fisher, ACS reagent), Florisil (Sigma-Aldrich, 100-200 mesh), hexanes (Fisher, ACS reagent, >98.5%), methyl t-butyl ether (Sigma-Aldrich, >98.5%).
10. The temperature rose as follows after the NaCN additions: #1, 18 to 28 °C; #2, 25 to 28 °C; #3, 24 to 25 °C.
11. Progress of the reaction was monitored by TLC (1:1 MTBE/hexanes) and visualized with UV light; Rf = 0.4 for product and 0.5 for starting material. The checker found the reaction achieved >95% completion by the current protocol. The submitters suggest that if complete conversion is not achieved, an additional portion of NaCN (0.25 equiv) and AcOH (3.2 mL) can be added and the reaction checked again after 20 min. If necessary, the water bath temperature can be raised to 50-55 °C in order to facilitate complete conversion.
12. Washing the organic phase with NaOH is designed to purge the solution of residual HCN. These precautions minimize the potential for contact with HCN during removal of solvent on a rotary evaporator that must be vented to, or located in, a fume hood. Residual NaCN is removed in the aq. washes, which should be treated with bleach prior to disposal.
13. Column chromatography on silica gel causes significant adsorption of the oxonitrile resulting in a low yield. However, the submitters found that 2 g of cyclohex-2-enone provided crude keto nitrile that was readily purified by radial chromatography (4 mm SiO2 plate, EtOAc/hexanes as eluent, 1:19) without significant adsorption. Concentration on a rotary evaporator provided pure 3-oxocyclohex-1-ene-carbonitrile (1.77 g, 70% yield over two steps).
14. Florisil (325 g) was wet-packed in a 7-cm diameter column using MTBE:hexanes (1:3) with a 0.5 cm bed of sand topping the column. The crude oil was loaded neat and rinsed onto the column with 2 x 5 mL MTBE. Elution was carried out with 1 L MTBE:hexanes (1:3), 1 L MTBE:hexanes (1:2), and 1 L of MTBE:hexanes (2:3). Column flow was 40 mL/min and 50 mL fractions were collected. Product elution was followed by TLC as indicated in Note 11. Fractions 33-50 were combined and concentrated by rotary evaporation (40 °C bath, 100 mmHg to 10 mmHg), then dried under vacuum (10 mmHg for 2 h) to constant weight to afford 7.20 g of a pale yellow oil. Purity by GC was 95 % (same conditions as Note 6, tR = 8.9 min). Fractions 30-32 and 51-60 were combined and likewise concentrated to 1.50 g. Purity by GC was 78%. These fractions were re-chromatographed using 100 g of Florisil, eluting with 300 mL MTBE:hexanes (1:3) and 600 mL MTBE:hexanes (1:2), collecting 25 mL fractions. Fractions 22-33 were combined and concentrated by rotary evaporation (40 °C bath, 100 mmHg to 10 mmHg), then vacuum dried to constant weight to afford 0.87 g of product. Purity by GC was 92%. The rich cuts from the two chromatographies were combined to afford product (8.07 g, 63% yield, GC purity 95%) as a pale yellow oil.
15. 3-Oxocyclohex-1-enecarbonitrile has the following spectroscopic properties: 1H NMR pdf (400 MHz, CDCl3) δ: 2.10-2.17 (m, 2 H), 2.49-2.53 (m, 2 H), 2.57 (td, J = 6.0, 2.0 Hz, 2 H), 6.52 (t, J = 2.0 Hz, 1 H); 13C NMR pdf (100 MHz, CDCl3) δ: 22.3, 27.8, 37.4, 117.2, 131.2, 138.9, 196.5. IR (neat) 3059, 2232, 1682, 1606 cm-1; HRMS calculated for C7H7NO 144.0420; found 144.0414 (M+Na)+. GC-MS m/z (rel intensity): 121 (M+, 68), 93 (100), 66 (27), 65 (38), 64 (30). After 4 months of storage at 4 °C the submitters found the sample underwent modest discoloration from light yellow to orange, although no loss of sample integrity was observed by 1H NMR and there was no change in reactivity.
Safety and Waste Disposal Information

The procedures in this article are intended for use only by persons with prior training in experimental organic chemistry. All hazardous materials should be handled using the standard procedures for work with chemicals described in references such as "Prudent Practices in the Laboratory" (The National Academies Press, Washington, D.C., 2011 www.nap.edu). All chemical waste should be disposed of in accordance with local regulations. For general guidelines for the management of chemical waste, see Chapter 8 of Prudent Practices.

These procedures must be conducted at one's own risk. Organic Syntheses, Inc., its Editors, and its Board of Directors do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein.

3. Discussion
Cyclic oxoalkenenitriles juxtapose three orthogonal functionalities capable of selective functionalization; an olefin, a ketone, and a nitrile functionality.5 3-Oxocycloalkenecarbonitriles, in particular, are excellent scaffolds for diversity oriented synthesis,6 feature strategically in syntheses,7 and as precursors for mechanistic studies.8 The electron deficient olefin in 3-oxocyclohex-1-ene-1-carbonitrile (Scheme 1, 1) is an excellent participant in [2+2]9 (1 2 and 1 3) and [4+2]10 cycloadditions (1 4), and in conjugate additions (1 → 5).11 Sequential addition of two Grignard reagents to 3-oxocyclohex-1-ene-1-carbonitrile (1) allows stepwise 1,2-1,4-additions to afford the extremely versatile C-magnesiated nitrile 5.11 Stereoselective annulations12 provide access to bicyclic and tricyclic nitriles 611 and 7,6 whereas complementary alkylation strategies access nitriles 8 and 9 bearingdiastereomeric, quaternary centers,13 and allow N-alkylation to enamides 10.14
Scheme 1. Synthetic Applications of 3-Oxocyclohex-1-enecarbonitrile (1)
The value of 3-Oxocyclohex-1-ene-1-carbonitrile (1) has stimulated several syntheses: cyanide addition to 1,3-cyclohexandione monoethylene ketal,15 Et2AlCN addition to 3-methoxycyclohexenone,16 or to cyclohexenone followed by periodinane oxidation,17 oxidative transposition of an allylic cyanohydrin,18 and allylic oxidation of cyclohexenecarbonitrile with PhI(OAc)2 and t-BuOOH,19 or with CrO3 and 3,5-dimethylpyrazole.3 Among strategies for synthesizing 1,3, 14, 15, 16, 17, 18, 19 and related sequences employed in total synthesis campaigns,7 the bromination-cyanation of cyclic enones20 is conspicuous for efficiency, cost, and operational simplicity (Scheme 2). Formation of 2-bromocyclohex-2-enone (12) from cyclohexenone (11) is fast and virtually quantitative. The subsequent conjugate addition of cyanide provides an intermediate ketone 13 from which dehydrohalogenation is readily achieved simply through modest heating. The synthesis of 3-Oxocyclohex-1-ene-1-carbonitrile (1) is very expedient and inexpensive. Operationally, the reaction uses standard glassware and affords gram quantities of 3-Oxocyclohex-1-ene-1-carbonitrile (1) from cyclohexenone in 2-steps that can be completed in one day.
Scheme 2. Synthesis of 3-Oxocyclohex-1-enecarbonitrile (1)
Employing the bromination-cyanation sequence with the homolog cycloheptenone (14) affords the seven-membered 3-oxocyclohept-1-ene-1-carbonitrile (Scheme3, 16).8b, 18, 21 The bromination of cycloheptenone (14) parallels the bromination of cyclohexenone (11), although the elimination of the intermediate dibromide requires heating the reaction mixture for 30 min at 70 °C to form 2-bromocyclohept-2-enone (15). Control over the temperature required for the elimination of HBr during the formation of 2-bromocyclohept-2-enone (15) is critical. The temperature was conveniently controlled using microwave irradiation,22 which reproducibly affords very pure 2-bromocyclohept-2-enone. Subsequent cyanation-elimination affords 3-oxocyclohept-1-enecarbonitrile (16) in 71% yield over two steps. The resulting 3-oxocyclohept-1-enecarbonitrile functionality has been strategically employed in total synthesis20 and is a valuable partner for sequential 1,2-1,4-addition-alkylations.21
Scheme 3. Synthesis of 3-Oxocyclohept-1-ene-1-carbonitrile (16)
Collectively, the bromination-cyanation of cyclic enones provides efficient, cost-effective syntheses of 3-oxocycloalkene-1-carbonitriles. The syntheses are rapid and provide access to functionalized building blocks ideally suited for synthetic applications.

References and Notes
  1. Department of Chemistry, Duquesne University, Pittsburgh, PA 15282-1530, email: flemingf@duq.edu. This work was supported by the National Science Foundation (CHE 1111406) and in part by CONACYT (J. A. L.-M.). Drew Davic is thanked for assistance in performing GCMS.
  2. For the reaction of hypochlorite solutions with cyanide, see the following reference and references therein: Gerritsen, C. M.; Margerum, D. W. Inorg. Chem. 1990, 29, 2757-2762.
  3. Fleming, F. F.; Zhang, Z.; Wei, G. Synthesis 2005, 3179-3180.
  4. For a previously reported mp of 72.5-75 °C see: Shih, C. J. Org. Chem. 1980, 45, 4462-4471; mp 75-76 °C reported by Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088-5093.
  5. Fleming, F. F.; Iyer, P. S. Synthesis 2006, 893-913.
  6. (a) Oguri, H.; Hiruma, T.; Yamagishi, Y.; Oikawa, H.; Ishiyama, A.; Otoguro, K.; Yamada, H.; Omura, S. J. Am. Chem. Soc. 2011, 133, 7096-7105. (b) Oguri, H.; Yamagishi, Y.; Hiruma, T.; Oikawa, H. Org. Lett. 2009, 11, 601-604.
  7. (a) Fleming, F. F.; Wei, G.; Steward, O. W. J. Org. Chem. 2008, 73, 3674-3679. (b) Morita, M.; Sone, T.; Ymatsugu, K.; Sohtome, Y.; Matsunaga, S.; Kanai, M.; Watanabe, Y.; Shibasaki, M. Bioorg. Medicinal Chem. Lett. 2008, 18, 600-602. (c) Yamatsugu, K.; Kamijo, S.; Suto, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2007, 48, 1403-1406. (d) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312-6313. (e) Jansen, J. H. M.; Lugtenburg, J. Eur. J. Org. Chem. 2000, 829-836. (f) Kutney, J. P.; Gunning, P. J.; Clewly, R. G.; Somerville, J.; Rettig, S. J. Can. J. Chem. 1992, 70, 2094-2114.
  8. (a) Klärner, F.-G.; Wurche, F.; von E. Doering, W.; Yang, J. J. Am. Chem. Soc. 2005, 127, 18107-18113. (b) Mease, R. C.; Hirsch, J. A. J. Org. Chem. 1984, 49, 2925-2937.
  9. (a) Cantrell, T. S. Tetrahedron 1971, 27, 1227-1237. (b) Agosta, W. C.; Lowrance, W. W. Jr. Tetrahedron Lett. 1969, 3053-3054.
  10. Yang, W. Q.; Chen, S. Z.; Huang, L. Chin. Chem. Lett. 1998, 9, 233-234.
  11. (a) Fleming, F. F.; Wei, Y.; Liu, W.; Zhang, Z. Tetrahedron 2008, 64, 7477-7488. (b) Fleming, F. F.; Wei, Y.; Liu, W.; Zhang, Z. Org. Lett. 2007, 9, 2733-2736. (c) Fleming, F. F.; Zhang, Z.; Wang, Q.; Steward, O. W. Angew. Chem., Int. Ed. 2004, 43, 1126-1129.
  12. Fleming, F. F.; Gudipati, S. Eur. J. Org. Chem. 2008, 5365-5374.
  13. (a) Fleming, F. F.; Zhang, Z.; Wei, G.; Steward, O. W. J. Org. Chem. 2006, 71, 1430-1435. (b) Fleming, F. F.; Zhang, Z.; Wei, G.; Steward, O. W. Org. Lett. 2005, 7, 447-449.
  14. Fleming, F. F.; Wei, G.; Zhang, Z.; Steward, O. W. Org. Lett. 2006, 8, 4903-4906.
  15. (a) Wang, Y.; Doering, W. v. E.; Staples, R. J. J. Chem. Crystallogr. 1999, 29, 977-982. (b) Cronyn, M. W.; Goodrich, J. E. J. Am. Chem. Soc. 1952, 74, 3331-3333.
  16. Agosta, W. C.; Lowrance, W. W. J. Org. Chem. 1970, 35, 3851-3856.
  17. Nicolaou, K. C.; Gray, D. L. F.; Montagnon, T.; Harrison, S. T. Angew. Chem., Int. Ed. 2002, 41, 996-1000
  18. Hudlicky, J. R.; Werner, L.; Semak, V.; Simionescu, R.; Hudlicky, T. Can. J. Chem. 2011, 89, 535-543.
  19. Zhao, Y.; Yeung, Y.-Y. Org. Lett. 2010, 12, 2128-2131.
  20. (a) Campos, K. R.; Klapars, A.; Kohmura, Y.; Pollard, D.; Ishibashi, H.; Kato, S.; Takezawa, A.; Waldman, J. H.; Wallace, D. J.; Chen, C.-y.; Yasuda, N. Org. Lett. 2011, 13, 1004-1007. (b) Ohmori, N. J. Chem. Soc., Perkin Trans. 1, 2002, 755-767. (c) Magnus, P.; Waring, M. J.; Ollivier, C.; Lynch, V. Tetrahedron Lett. 2001, 42, 4947-4950. (d) Ohmori, N. Chem. Commun. 2001 1552-1553. (e) Isobe, M.; Nishikawa, T.; Pikul, S.; Goto, T. Tetrahedron Lett. 1987, 28, 6485-6488. (f) Audenaert, F.; De Keukeleire, D.; Vandewalle, M. Tetrahedron 1987, 43, 5593-5604.
  21. Fleming, F. F.; Wei, G.; Zhang, Z.; Steward, O. W. J. Org. Chem. 2007, 72, 5270-5275.
  22. A Biotage® microwave reactor (Model: Initiator) and a 20 mL reaction tube was used in a reaction employing 1.8 g of cyclohept-2-enone. The radiation absorption parameter was set to NORMAL, with the apparatus initially recording a slight increase of pressure (2 - 3 Psi).

Chemical Abstracts Nomenclature; (Registry Number)

2-Bromo-2-cyclohexen-1-one (12); (50870-61-6)

Cyclohex-2-enone (11); (930-68-7)

3-Oxocyclohex-1-enecarbonitrile (1); (25017-78-1)

Fraser Fleming earned his B. Sc. (Hons.) at Massey University, New Zealand, in 1986 and a Ph. D. under the direction of Edward Piers at the University of British Columbia, Canada, in 1990. After postdoctoral research with James D. White at Oregon State University he joined the faculty at Duquesne University, Pittsburgh, in 1992. His research interests lie in stereochemistry and organometallics, particularly as applied to alkenenitrile conjugate additions and metalated nitrile alkylations.
Jesus Armando Lujan-Montelongo, a native of Queretaro, Mexico, completed his BS at the National University Autonomous of Mexico (UNAM) in 2003. He continued his studies at UNAM, earning his Ph. D. in Organic Chemistry in 2005 under the direction of Jose G. Avila-Zarraga. After postdoctoral studies with Luis Miranda at the Institute of Chemistry (UNAM) developing free-radical based synthetic methods, he joined Fraser Fleming at Duquesne University in Pittsburgh, where he is working on nitrile-based methodology. His research interests lie in the total synthesis of natural products and in organometallic chemistry.