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Zur Photochemie des Benzfurazans
Author(s) -
Georgarakis M.,
Rosenkranz H. J.,
Schmid H.
Publication year - 1971
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.19710540306
Subject(s) - chemistry , methanol , nitrene , nitrile , benzene , azepine , medicinal chemistry , derivative (finance) , irradiation , oxide , carbamate , photochemistry , organic chemistry , catalysis , physics , nuclear physics , financial economics , economics
Irradiation of benzofurazan ( 1 ) in benzene solution yields the azepine derivative 3 as the main photoproduct. Addition of methanol in the dark to the irradiated benzene solution of 1 results in the isolation of 3 together with a new product, methyl‐1‐ cis , 3‐ cis ‐N‐(4‐cyano‐buta‐1, 3‐dien‐1‐yl)‐carbamate (1‐ cis , 3‐ cis ‐ 2 ). Irradiation of 1 in methanol solution gives a mixture of the stereoisomeric methyl N‐(4‐cyano‐buta‐1, 3‐dien‐1‐yl)‐carbamates, from which the 1‐ trans , 3‐ cis isomer of 2 could be isolated in pure form. The observed photoproducts are formed via the reactive intermediates a , a nitrile‐(nitrile oxide), and c , a nitrene, neither of which was isolated.