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Synthesis of thiophene-2-phosphonates via α,β-unsaturated sulfines as intermediates

✍ Scribed by Johannes B. van der Linden; André C. B. Lucassen; Binne Zwanenburg

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
524 KB
Volume
113
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Heteroconjugate addition of various alkyllithium reagents to α‐silylallenephosphonates 3b,c has been accomplished in high yields. The formation of thiophene‐2‐phosphonates 5, by heteroconjugate addition of organolithium to 3bc, followed by treatment with sulfur dioxide, proceeds in reasonable yields via the intermediate formation of α,β‐unsaturated sulfines 4. An alternative synthesis of the heteroconjugate addition product diethyl 1‐(trimethylsily)‐2,3‐dimethylbut‐2‐ene‐1‐phosphonate 6a from 2,3‐dimethylbut‐2‐enyl bromide has also been described.

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