✦ LIBER ✦

Photochemical Cyclization of Allylated Anisole and N-Alkyl Aniline Derivatives. Preliminary communication

✍ Scribed by Ursula Koch-Pomeranz; Hans-Jürgen Hansen; Hans Schmid

Publisher: John Wiley and Sons
Year: 1975
Tongue: German
Weight: 255 KB
Volume: 58
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19750580122

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✦ Synopsis

Abstract

The allyl anisole derivatives 1, d~2~‐1, 3, 5 and 7 (Scheme 1), on exposure to UV. light in benzene, acetone or methanol solution, cyclize to yield the corresponding cyclopropyl anisole derivatives 2, d~2~‐2, cis‐ and trans‐4, 6 and 8, respectively. Under the above conditions the N, N‐dialkyl‐2‐allyl anilines 9, 10 and 11 give similar results (Scheme 2). On the other hand, N‐alkyl‐2‐allyl anilines (15 and 19, Scheme 3) are transformed by UV. light in cyclohexane or benzene solution into 2‐methyl‐indolines (16 and 20, resp.), whereas in methanol solution the corresponding 2′‐methoxy compounds 18 and 21 are formed in addition to 16 and 20, respectively.

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