Issue 10, 1978
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Vinyl carbanions. Part 4. Use of vinyl carbanions derived from ββ-diphenylacrylonitrile as nucleophiles

Uri Melamed  and  Ben A. Feit  

Abstract

Vinyl carbanions of the type Ph2C[double bond, length half m-dash][C with combining macron]·CN (1a) were formed by treating ββ-diphenylacrylonitrile (1) with BuLi in tetrahydrofuran, at –78 °C. These vinyl carbanions were applied as nucleophiles in addition and SN-type reactions with the following electrophiles: ββ-diphenylacrylonitrile, benzophenone, trans-α-cyanostilbene, carbon dioxide, and alkyl iodides. The addition of (1a) to (1) took place at C(α) and afforded the addition product 1,1,4,4-tetraphenyl-2,3-dicyanobut-1-ene, and the addition–elimination products 1,1,4,4-tetraphenyl-2-cyanobutadiene and 1,1,4,4-tetraphenyl-2-butyl-3-cyanobut-1-ene. With trans-α-cyanostilbene, the Michael addition product was formed. A common by-product in all reactions was 1,1-diphenylhex-1-ene.

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/P19780001232
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1978, 1232-1236

Permissions

Request permissions

Vinyl carbanions. Part 4. Use of vinyl carbanions derived from ββ-diphenylacrylonitrile as nucleophiles

U. Melamed and B. A. Feit, J. Chem. Soc., Perkin Trans. 1, 1978, 1232 DOI: 10.1039/P19780001232

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements