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Use of 1-Chlorovinyl p-Tolyl Sulfoxides as Alkynylmagnesium Chloride Sources

14 February 2023, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A method for generating alkynylmagnesium chlorides from 1-chlorovinyl p-tolyl sulfoxides and an isopropylmagnesium chloride-lithium chloride complex (turbo Grignard reagent) has been developed. The method consists of a sulfoxide/magnesium exchange reaction of 1-chlorovinyl p-tolyl sulfoxides and a turbo Grignard reagent, a FritschButtenbergWiechell rearrangement of the resulting magnesium alkylidene carbenoids, and a deprotonation of terminal alkynes with a turbo Grignard reagent. The resulting alkynylmagnesium chlorides are reacted with a variety of electrophiles to generate internal alkynes.

Keywords

alkynes
alkynylmagnesium chlorides
1-chlorovinyl p-tolyl sulfoxides
Fritsch–Buttenberg–Wiechell rearrangement
magnesium alkylidene carbenoids
sulfoxide/magnesium exchange reaction
nucleophilic alkynyllation

Supplementary materials

Title
Description
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Supporting Information
Description
1H and 13C NMR spectra (PDF)
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Version History

Feb 14, 2023 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-xbgkd
D O I: 10.26434/chemrxiv-2023-xbgkd [opens in a new tab]

Funding

Japan Society for the Promotion of Science
18K05129

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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