✦ LIBER ✦

Preparation and Electrophilic Substitution of 1-Trimethylsilylpentadienyllithium

✍ Scribed by Wolfgang Oppolzer; Sidney C. Burford; Fabrizio Marazza

Book ID: 102858467
Publisher: John Wiley and Sons
Year: 1980
Tongue: German
Weight: 528 KB
Volume: 63
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19800630302

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✦ Synopsis

Abstract

Pentadienyllithium (16) was regioselectively and efficiently transformed to 1‐trimethylsilyl‐2,4‐pentadiene (17) by reaction with chlorotrimethylsilane (Scheme 5). Deprotonation of 17 and subsequent electrophilic attack furnished the regioisomeric products 12 and/or 13 in good yields (Schemes 5 and 6). The utility of the reaction 18→12 for the convergent assembly of the 1‐silyl‐1,3‐butadiene unit with an olefinic dienophile is further illustrated by the smooth intramolecular Diels‐Alder reaction 19→20.

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