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A new method for the synthesis of 2-phenylsulfonylaziridines via the reaction of α-halosulfonyl carbanion to imines

✍ Scribed by Vichai Reutrakul; Vichukorn Prapansiri; Chitchanun Panyachotipun

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
194 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of lithio a-chloromethyl phenyl sulfone with imines gave aziridines in good yields. The resulting aziridines were alkylated and underwent the 1,3-dipolar cycloaddition with dimethylacetylene dicarboxylate to give pyrroles in excellent yields. Much attention has been focused on the chemistry of the a-sulfonyl carbanion due to its immense applications in organic synthesis'. In addition to its ability to stabilize the adjacent n anionic centre, the sulfonyl group can also be removed under very mild conditionL. Recent work on the a-halosulfonyl carbanion3 also indicated that this species can undergo alkylation and addition reactions to give synthetically useful intermediates.

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