Publications

GROUP PUBLICATIONS

 

(54) “Oxygen-Substituted Isocyanates: Blocked (Masked) Isocyanates Enable Controlled Reactivity” Ivanovich, R. I.; Polat, D. E.; Beauchemin, A. M. Adv. Synth. Catal. 2017 369 Early View [link]. (Selected as VIP)

(53) ” Synthesis of Indazolones via Friedel−Crafts Cyclization of Blocked (Masked) N‑Isocyanates” Elkaeed, E. B.; An, J.; Beauchemin, A. M. J. Org. Chem. 2017 ASAP [link].

(52) “o-Phthalaldehyde Catalyzed Hydrolysis of Organophosphinic Amides and Other P([double bond, length as m-dash]O)–NH Containing Compounds” Li, B.-J.; Simard, R. D.; Beauchemin, A. M. Chem. Commun. 2017, 53,  8667 – 8670 [link].

(51) “On the Ability of Formaldehyde to act as a Tethering Catalyst in Water” Jamshidi, M. P.; MacDonald, M. J.; Beauchemin, A. M. Orig. Life Evol. Biosph. 2017, ASAP [link].

(50) “Intermolecular Aminocarbonlyation of Alkenes using Concerted Cycloadditions of Iminoisocyanates” Bongers, A. B.; Clavette, C.; Gan, W.; Gorelsky, S. I.; Betit, L.; Lavergne, K.; Markiewicz, T.; Moon, P. J.; Das Neves, N.; Obhi, N. K.; Toderian, A. B.; Beauchemin, A. M. J. Org. Chem. 2017, 82 , 1175–1194 [link].

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(49) “A Cascade Synthesis of 1,2,4,-Triazin-3(2H)-ones using  Nitrogen-Substituted Isocyanates” Dahab, M. A.; Derasp, J. S.; Beauchemin, A. M. Synlett 2017, 28, 456-460 [link]. (Invited contribution)

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(48) “Carbohydrates as Efficient Catalysts for the Hydration of alpha-Amino Nitriles” Chitale, S.; Derasp, J. S.; Hussain, B.; Tanveer, K.; Beauchemin, A. M. Chem. Commun. 2016, 52, 13147-13150 [link].

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(47) “N-Isocyanates, N-Isothiocyanates and Their Masked/Blocked Derivatives: Synthesis and Reactivity” Vincent-Rocan, J.-F.; Beauchemin, A. M. Synthesis 2016, 48, 3625-3645 [link]. (Invited contribution)toc-47

(46) “Synthesis of Cyclic Azomethine Imines by Cycloaddition Reactions of N-Isocyanates and N-Isothiocyanates” Bongers, A.; Ranasinghe, I.; Lemire, P.; Perozzo, A.; Vincent-Rocan, J.-F.; Beauchemin, A. M. Org. Lett. 2016, 18, 3778-3781 [link].

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(45) “Copper-Catalyzed Cascade Substitution/Cyclization of N-Isocyanates: A Synthesis of 1-Aminobenzimidazolones” An, J.; Alper, H.; Beauchemin, A. M. Org. Lett. 2016, 18, 3482-3485 [link].

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(44) “Intramolecular Alkene Aminocarbonylation Using Concerted Cycloadditions of Amino-Isocyanates” Ivanovich, R. A.; Clavette, C.; Vincent-Rocan, J.-F.; Roveda, J.-G.; Gorelsky, S. I.; Beauchemin, A. M. Chem. Eur. J. 2016, 22, 7906-7916 [link]. ( hotSelected as Hot Paper)

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(43) “Divergent Reactivity of N-Isocyanates with Primary and Secondary Amines: Access to Pyridazinones and Triazinones” Derasp, J. S.; Vincent-Rocan, J.-F.; Beauchemin, A. M. Org. Lett2016, 18,  658661 [link].

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(42) “Cascade Reactions of Nitrogen-Substituted Isocyanates: A New Tool In Heterocyclic Chemistry” Vincent-Rocan, J.-F.; Ivanovich, R. A.; Clavette, C.; Leckett, K.; Bejjiani, J.; Beauchemin, A. M. Chem. Sci. 20167, 315-328 [link]. (Highlighted in Org. Process Res. Dev. 2016, 20, 105-122)

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(41) “Kinetic Resolution of Azomethine Imines by Brønsted Acid Catalyzed Enantioselective Reduction” Bongers, A.; Moon, P. J.; Beauchemin, A. M. Angew. Chem. Int. Ed.  2015, 54, 15516 – 15519 [link]. 

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(40) “Formaldehyde as Tethering Organocatalyst: Highly Diastereoselective Hydroaminations of Allylic Amines” Hesp, C. R.; MacDonald, M.; Zahedi, M.; Bilodeau, D. A.; Zhao, S.-B.; Pesant, M.; Beauchemin, A. M. Org. Lett. 2015, 17, 5136 – 5139 [link].

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(39) “One-Pot Synthesis of Aza-Diketopiperazines Enabled by Controlled Reactivity of N‑Isocyanate Precursors” Ivanovich, R. A.; Vincent-Rocan, J.-F.; Elkaeed, E. B.; Beauchemin, A. M. Org. Lett. 2015,  17, 4898 – 4901 [link].

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(38) “Diversity Oriented Heterocyclic Synthesis using Divergent Reactivity of N-Substituted Iso(thio)cyanates” Vincent-Rocan, J.-F.; Derasp, J.  S.; Beauchemin, A. M. Chem. Commun. 2015, 51, 16405 – 16408 [link].

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(37) “Modular Synthesis of Pyrazolones Using an Alkene Aminocarbonylation Reaction” Lavergne, K.; Bongers, A.; Betit, L.;  Beauchemin, A. M. Org. Lett. 201517,  3612–3615 [link].

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(36) “A Cascade Synthesis of Aminohydantoins Using In Situ-Generated N-Substituted Isocyanates” Vincent-Rocan, J.-F.; Clavette, C.; Leckett, K.; Beauchemin, A. M. Chem. Eur. J. 2015, 21, 3886 – 3890 [link]. (hot Selected as Hot Paper)

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(35) “Photocatalytic Generation of N-Centered Hydrazonyl Radicals: A Strategy for Hydroamination of beta,gamma-Unsaturated Hydrazones” Hu, Q.-X.; Chen, J.-R.; Wei, Q.; Liu, F.-L.; Deng, Q.-H.; Beauchemin, A. M.; Xiao, W.-J. Angew. Chem. Int. Ed. 2014, 53, 12163–12167 [link]. (Collaboration with the Xiao research group)

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(34) “Stereoelectronic Basis for the Kinetic Resolution of N-Heterocycles with Chiral Acylating Reagents” Hsieh, S.-Y.; Wanner, B.; Wheeler, P.; Beauchemin, A. M.; Rovis, T.; Bode, J.-W. Chem. Eur. J. 2014, 20, 7228 – 7231 [link]. (Collaboration with the Bode research group)

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(33) “Expedient Synthesis of 2-Oxopiperazines Using a SN2 / Cope-Type Hydroamination Sequence” Das Neves, N.; Raymond, M.; Beauchemin, A. M. Heterocycles 2014, 88, 639-650 [DOI: 10.3987/COM-13-S(S)18].

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(32) “Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products” Dion, I.; Vincent-Rocan, J.-F.; Zhang, L.; Cebrowski, P. H.; Lebrun, M.-E.; Pfeiffer, J. Y.; Bédard, A.-C.; Beauchemin, A. M. J. Org. Chem. 2013, 78, 12735-12749 [link].

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 (31) “Diversity-Oriented Synthesis of Hydrazine-Derived Compounds via Amino-Isocyanates” Clavette, C.; Vincent-Rocan, J.-F.; Beauchemin, A. M. Angew. Chem. Int. Ed. 2013, 52, 12705-12708 [link].

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(30) “Recent developments in Cope-type hydroamination reactions of hydroxylamine and hydrazine derivatives” Beauchemin, A. M. Org. Biomol. Chem. 2013, 11, 7039-7050 [link].

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(29) “Exploiting Intramolecularity” Beauchemin, A. M. Nature Chemistry 2013, 5, 731-732 [link]. (Invited highlight)

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(28) “A Practical Approach to Semicarbazones and Hydrazones Derivatives via Imino-Isocyanates” Garland, K.; Gan, W.; Depatie-Sicard, C.; Beauchemin, A. M. Org. Lett. 2013, 15, 4074-4077 [link].

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(27) “Synthesis of Azomethine Imines Using an Intramolecular Alkyne Hydrohydrazination Approach” Hunt, A. D.; Dion, I.; Das Neves, N.; Taing, S.; Beauchemin, A. M. J. Org. Chem. 2013, 78, 8847-8852 [link].

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(26) “Rearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry” Chigrinova, M.; McKay, C. S.; Beaulieu, L.-P. B.; Oudatchin, K. A.; Beauchemin, A. M.; Pezacki, J. P. Org. Biomol. Chem. 2013,11, 3436-3441 [link]. (Collaboration with the Pezacki group)

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(25) “Synthesis and Reactivity of Unsymmetrical Azomethine Imines Formed Using Alkene Aminocarbonylation” Gan, W.; Moon, P.; Clavette, C.; DasNeves, N.; Markiewicz, T.; Toderian, A.; Beauchemin, A. M. Org. Lett. 2013, 15, 1890-1893 [link].

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(24) “Turning on Single-Molecule Behavior in a Linear [Mn3] Compound ” Habib, F.; Brunet, G.; Loiseau, F.; Pathmalingam, T.; Burchell, T. J.; Beauchemin, A. M.; Wernsdorfer, W.; Clérac, R.; Murugesu, M. Inorg. Chem. 2013, 52, 1296-1303 [link]. (Collaboration with the Murugesu research group)

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(23) “Highly Enantioselective Intermolecular Hydroaminations of Allylic Amines Using Chiral Aldehydes as Tethering Catalysts” MacDonald, M. J.; Hesp, C. R.; Schipper, D. J.; Pesant, M.; Beauchemin, A. M. Chem. Eur. J. 2013, 19, 2597-2601 [link].

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(22) “Intermolecular retro-Cope Hydroxylamination of Alkynes with NH2OH: (E-1-(1-Hydroxycyclohexyl)ethanone oxime)” Loiseau, F.; Beauchemin, A. M. Org. Synth. 2013, 90, 87-95 [link].

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(21) “Hydrogen Bonding-Directed Intermolecular Cope-Type Hydroamination of Alkenes ” Zhao, S.; Bilodeau, E.; Lemieux, V.; Beauchemin, A. M. Org. Lett. 2012, 14, 5082-5085 [link].

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(20) “A Tunable Route for the Synthesis of Azomethine Imines and β-Aminocarbonyl Compounds from Alkenes” Clavette, C.; Gan, W.; Bongers, A.; Markiewicz, T.; Toderian, A.; Gorelsky, S. I.; Beauchemin, A. M. J. Am. Chem. Soc. 2012, 134, 16111-16114 [link]. (Highlighted in Synfacts)

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(19) “Catalysis through temporary intramolecularity: Mechanistic Investigations on Aldehyde-Catalyzed Cope-Type hydroamination lead to the discovery of a more efficient tethering catalyst” Guimond, N.; MacDonald, M. J.; Lemieux, V.; Beauchemin, A. M. J. Am. Chem. Soc. 2012, 134, 16571-16577 [link].

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(18) “A Novel High-Spin Tridecanuclear Ni(II) Cluster with an Azido-Bridged Core Exhibiting Disk-Like Topology” Brunet, G.; Habib, F.; Cook, C.; Pathmalingam, T.; Loiseau, F.; Korobkov, I.; Burchell, T. J.; Beauchemin, A. M.; Murugesu, M. Chem. Comm. 2012, 48, 1287-1289 [link]. (Collaboration with the Murugesu research group)

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(17) “A Catalytic Tethering Strategy: Simple Aldehydes Catalyze Intermolecular Alkene Hydroaminations” MacDonald, M. J.; Schipper, D. J.; Ng, P. J.; Moran, J.; Beauchemin, A.M. J. Am. Chem. Soc. 2011, 133, 20100-20103 [link]. (Highlighted in Nature Chemistry and Synfacts)

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(16) “Asymmetric Bronsted Acid Catalysis Enabling Hydroaminations of Dienes and Allenes” Dion, I.; Beauchemin, A. M. Angew. Chem., Int. Ed. 2011, 50, 8233-8235 [link]. (Invited highlight)

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(15) “Improved Cope-Type Hydroamination Reactivity of Hydrazine Derivatives ” Loiseau, F.; Clavette, C.; Raymond, M.; Roveda, J.-G.; Burrell, A.; Beauchemin, A. M. Chem. Comm. 2011, 47, 562-564 [link]. (Invited contribution)

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(14) “Combining Oximes with Azides to Create a Novel 1-D[NaCoIII2] System: Synthesis, Structure, and Solid-State NMR” Pathmalingam, T.; Habib, F.; Widdifield, C. M.; Loiseau, F.; Burchell, T. J.; Gorelsky, S. I.; Beauchemin, A. M.; Bryce, D. L.; Murugesu, M. Dalton Trans. 2010, 39, 1504-1510 [link]. (Collaboration with the Murugesu and Bryce research groups)

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(13) “Simple Reaction Conditions for the Formation of Ketonitrones from Ketones and Hydroxylamines” Pfeiffer, J. Y., Beauchemin, A. M. J. Org. Chem. 2009, 74, 8381-8383 [link].

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(12) “Synthesis of Pyridines and Pyrazines Using an Intramolecular Hydroamination-Based Sequence” Rizk, T.; Bilodeau, E. J.-F.; Beauchemin, A. M. Angew. Chem., Int. Ed. 2009, 48, 8325-8327 [link]. (Highlighted in Synfacts)

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(11) “Hydrazides as Tunable Reagents for Alkene Hydroamination and Aminocarbonylation” Roveda, J. G.; Clavette, C.; Hunt, A. D.; Gorelsky, S. I.; Whipp, C. J.; Beauchemin, A. M. J. Am. Chem. Soc. 2009, 131, 8740-8741 [link]. (Highlighted in Synfacts)

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(10) “Ketonitrones via Cope-Type Hydroamination of Allenes” Moran, J.; Pfeiffer, J. Y.; Gorelsky, S. I.; Beauchemin, A. M. Org. Lett. 2009, 11, 1895-1898 [link].

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(9) “Synthesis of 2-epi-Pumiliotoxin C Via a Challenging Intramolecular Hydroamination Key Step” Lebrun, M.-E.; Pfeiffer, J. Y.; Beauchemin, A. M. Synlett 2009, 1087-1090 [link].

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(8) “The Tandem Cope-Type Hydroamination / [2,3]-Rearrangement Sequence: A Strategy to Favour the Formation of Intermolecular Hydroamination Products and Enable Difficult Cyclizations” Bourgeois, J.; Dion, I.; Cebrowski, P. H.; Loiseau, F.; Bédard, A.-C.; Beauchemin, A. M. J. Am. Chem. Soc. 2009, 131, 874-875 [link].

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(7) “Intermolecular Cope-Type Hydroamination of Alkenes and Alkynes Using Hydroxylamines” Moran, J.; Gorelsky, S. I.; Dimitrijevic, E.; Lebrun, M.-E.; Bédard, A.-C.; Séguin, C.; Beauchemin, A. M. J. Am. Chem. Soc. 2008, 130, 17893-17906 [link].

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(6) “A Rare Ligand Bridged Ferromagnetically Coupled Mn(IV)3 Complex with S = 9/2” Pathmalingam, T.; Gorelsky, S. I.; Burchell, T. J.; Bédard, A.-C.; Beauchemin, A. M.; Clérac, R.; Murugesu, M. Chem. Commun. 2008, 2782-2784 [link]. (Collaboration with the Murugesu research group)

(5) “Intermolecular Cope-Type Hydroamination of Alkynes Using Hydrazines” Cebrowski, P. H.; Roveda, J.-G.; Moran, J.; Gorelsky, S. I.; Beauchemin, A. M. Chem. Commun. 2008, 492-493 [link].

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(4) “Intermolecular Cope-Type Hydroamination of Alkenes and Alkynes” Beauchemin, A. M.; Moran, J.; Lebrun, M.-E.; Séguin, C.; Dimitrijevic, E.; Zhang, L.; Gorelsky, S. I. Angew. Chem., Int. Ed. 2008, 47, 1410-1413 [link].

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(3) “Intermolecular Hydroaminations via Strained E-Cycloalkenes” Moran, J.; Cebrowski, P. H.; Beauchemin, A. M. J. Org. Chem. 2008, 73, 1004-1007 [link].

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(2) “Strain-release Electrophilic Activation via E-Cycloalkenones” Moran, J.; Dornan, P.; Beauchemin, A. M. Org. Lett. 2007, 9, 3893-3896 [link].

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(1) “Photoinduced 1,4-Addition of Indoles to Enones” Moran, J.; Suen, T.; Beauchemin, A. M. J. Org. Chem. 2006, 71, 676-679 [link].

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PREVIOUS PUBLICATIONS

“Total Synthesis of (+)-Azaspiracid-1. An Exhibition of the Intricacies of Complex Molecule Synthesis” Evans, D. A.; Dunn, T. B.; Kvaerno, L.; Beauchemin, A.; Raymer, B.; Olhava, E. J.; Mulder, J. A.; Juhl, M.; Kagechika, K.; Favor, D. A. J. Am. Chem. Soc. 2008, 130, 16295-16309.

“Total Synthesis of (+)-Azaspiracid-1. Part II: Synthesis of the EFGHI- Sulfone and Completion of the Synthesis” Evans, D. A.; Dunn, T. B.; Kvaerno, L.; Beauchemin, A.; Raymer, B.; Olhava, E. J.; Mulder, J. A.; Juhl, M.; Kagechika, K.; Favor, D. A. Angew. Chem., Int. Ed. 2007, 46, 4698-4703.

“Total Synthesis of (+)-Azaspiracid-1. Part I: Synthesis of the Fully Elaborated ABCD-Aldehyde” Evans, D. A.; Kvaerno, L.; Mulder, J. A.; Raymer, B.; Dunn, T. B.; Beauchemin, A.; Olhava, E. J.; Juhl, M.; Kagechika, K. Angew. Chem., Int. Ed. 2007, 46, 4693-4697.

“Photoinduced Alkyl Group Exchange of Ethylzinc Alkoxides: X-Ray Crystal Structure of an Iodomethylzinc Alkoxide” Charette, A. B.; Beauchemin, A.; Francoeur, S.; Bélanger-Gariépy, F.; Enright, G. D. Chem Commun. 2002, 466-467.

“Acyloxymethylzinc Reagents: Preparation, Reactivity and Solid-State Structure of this Novel Class of Cyclopropanating Reagents” Charette, A. B.; Beauchemin, A.; Francoeur, S. J. Am. Chem. Soc. 2001, 123, 8139-8140.

“The Simmons-Smith Cyclopropanation Reaction” Charette, A.B.; Beauchemin, A. Org. React. 2001, 58, 1-415.

“Reinvestigation of the Chemoselective Cyclopropanation of Allylic Alcohols, Allylic Ethers and Alkenes: a Comparison between Various Reagents and Protocols” Charette, A. B.; Beauchemin, A. J. Organomet. Chem. 2001, 617-618, 702-708.

“Preparation, Solid-State Structure, and Synthetic Applications of Isolable and Storable Haloalkylzinc Reagents” Charette, A. B.; Marcoux, J.-F.; Molinaro, C.; Beauchemin, A.; Brochu, C.; Isabel, E. J. Am. Chem. Soc. 2000, 122, 4508-4509.

“Preparation and Reactivity of Some Functionalized Halomethylzinc Carbenoids” Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. Tetrahedron Lett. 1999, 40, 33-36.

“Photoinduced Synthesis of Diorganozinc and Organozinc Iodide Reagents” Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114-5115.

“Free Radical Addition of Diisopropyl Xantogen Disulfide with Unsaturated Systems” Beauchemin, A.; Gareau, Y. Heterocycles 1998, 48, 2003-2017.

“Studies of Triphenylsilanethiol Addition to Alkynes: Preparation of Vinyl Sulfides” Beauchemin, A.; Gareau, Y. Phos., Sulfur and Silicon 1998, 139, 187-192.

“Simple Method for the Preparation of 1,3-Dithiol-2-one and 1,3-Dithiol-2-thione” Beauchemin, A.; Gareau, Y. Phos., Sulfur and Silicon 1997, 120-121, 393-394.