Betaine formation from the reactions of N-heterocyclic carbenes with polarized alkenes-Reference-Cited by-同舟云学术

Betaine formation from the reactions of N-heterocyclic carbenes with polarized alkenes

Published:2021-12-01 Issue: Volume: Page:
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Ghanbari Hamed¹,Robertson Katherine N.²,Clyburne Jason³,Soleimani Ebrahim⁴⁵⁶

Affiliation:

1. Razi University, 48494, Department of Chemistry, Kermanshah, Iran (the Islamic Republic of);

2. Saint Mary's University, Chemistry, 923 Robie Street, Halifax, Nova Scotia, Canada, B3H 3C3;

3. Saint Mary’s University, Department of Chemistry, Halifax, Canada, B3H 3C3;

4. Razi University, 48494, Department of Chemistry, Kermanshah, Iran (the Islamic Republic of)

5. Saint Mary’s University, Department of Chemistry, Halifax, Canada, B3H 3C3

6. Dalhousie University, 3688, Department of Chemistry, Halifax, Canada, B3H 4R2;

Abstract

N-heterocyclic carbenes [1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene 1a (IMes) or 1,3-bis(2,6-di-iso-propylphenyl)imidazolidene 1b (SIPr)] react with the polarized alkenes 2 and 4 to form the crystalline betaines 3a, 3b and 5a. Furthermore, a one-pot reaction between an aldehyde, malonitrile, and an imidazolium salt of an N-heterocyclic carbene has been developed for the efficient preparation of betaine 5a without isolation of the free carbene. Full characterization data, including X-ray crystal structures, is reported for the three synthesized betaines. The structures of the betaines 3a, 3b and 5a shed new light on the initial products formed in the reactions between N-heterocyclic carbenes and compounds containing polarized double bonds.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

https://cdnsciencepub.com/doi/pdf/10.1139/cjc-2021-0234