Synthesis of Vinyl Chlorides via Triphosgene-Pyridine Activation of Ketones | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

3491589

Reference Type

Journal Article

Title

Synthesis of Vinyl Chlorides via Triphosgene-Pyridine Activation of Ketones

Author(s)

Saputra, MA; Ngo, L; Kartika, R

Year

2015

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Publisher

American Chemical Society

Book Title

Journal of Organic Chemistry

Volume

Issue

Page Numbers

8815-8820

Language

English

PMID

26247230

DOI

10.1021/acs.joc.5b01137

Web of Science Id

WOS:000361087400036

URL

http://://WOS:000361087400036
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Abstract

Herein, we describe a mild method to prepare aliphatic and aromatic vinyl chlorides from their corresponding ketones via triphosgene-pyridine activation in dichloromethane at reflux. The mechanism of this reaction is proposed to involve formation of a putative α-chloro pyridinium carbamate intermediate, which appeared to readily undergo E2 elimination in the presence of pyridine.

Keywords

Chemical activation; Dichloromethane; Ketones; Pyridine; Reaction intermediates; Pyridinium; Triphosgene; Vinyl chlorides; Synthesis (chemical); alpha chloro pyridinium carbamate; ketone; phosgene; pyridine; unclassified drug; vinyl chloride; Article; chemical structure; elimination reaction; reaction optimization; synthesis