✦ LIBER ✦

The Chemistry of N-substituted benzotriazoles. Part 22 [1]: Transformations of 1-(trimethylsilylmethyl)benzotriazole

✍ Scribed by Alan R. Katritzky; Jamshed N. Lam

Book ID: 102846388
Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 838 KB
Volume: 1
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520010104

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✦ Synopsis

Abstract

1‐(Trimethylsilylmethyl)benzotriazole is readily prepared from benzotriazole and chloromethyltrimethylsilane. It undergoes fluoride‐catalyzed desilylation with carbonyl compounds and forms an anion that can be alkylated and acylated readily and undergoes Peterson olefination. 1‐(Cyclohexylidenemethyl)benzotriazole is lithiated exclusively at the α carbon atom, and the anion can be cleanly alkylated.

1‐(α‐Acylalkyl)benzotriazoles are reduced to ketones with zinc and acid. The stability of 1‐alkenylbenzotriazoles to hydrolysis has been studied.

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