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A convenient synthesis of 2-alkyl- and 2-aryl-1,3-benzodithioles

✍ Scribed by Smollie Ncube; Andrew Pelter; Keith Smith

Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
122 KB
Volume
18
Category
Article
ISSN
0040-4039

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✦ Synopsis

%Alkyl-and 2-aryl-1,3-benxodithioles are obtained in high yield by the reaction of Grignard reagents or lithium alkyls with 2-alkoxy-1,3-benaodithioles,themaelves available in one step from anthranilic acid.

In connection with our studies of the reactions of acyl carbanion equivalents with organoboranee', we had need of anions derived from 2-alkyl or 2-aryl-1,3-benxodithiolea (2).

We were surprised at the paucity of information available about such anions, indeed in the latest review of acyl carbanlon equivalents' they are not even mentioned-It was soon apparent that the reason for the small utlllsatlon of these attractive anions is that the compounds ( 2) are normally derived by reaction of aldehydes with benzene-1,2-dithiol, and the latter compound is available only by extremely tedious methods.

3

Recently, however, 2-alkoxy-1,3-benaodlthiolea (1) have become readily available by the action of benzyne (conveniently generated from anthranilic acid) on carbon dlaulphide in the

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