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Photochemical Cyclization of Allylated Anisole and N‐Alkyl Aniline Derivatives. Preliminary communication
Author(s) -
KochPomeranz Ursula,
Hansen HansJürgen,
Schmid Hans
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580122
Subject(s) - chemistry , anisole , benzene , cyclohexane , aniline , methanol , medicinal chemistry , acetone , yield (engineering) , alkyl , photochemistry , organic chemistry , catalysis , materials science , metallurgy
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.