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Formation of Bicyclic Pyrroles and Furans Through an Enone Allene Photocycloaddition and Fragmentation Sequence
Author(s) -
Lutteke Ginger,
AlHussainy Rana,
Wrigstedt Pauli J.,
Hue B. T. B.,
de Gelder René,
van Maarseveen Jan H.,
Hiemstra Henk
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701017
Subject(s) - chemistry , allene , bicyclic molecule , adduct , furan , enone , cycloaddition , pyrrole , medicinal chemistry , substituent , cyclohexene , fragmentation (computing) , photochemistry , stereochemistry , organic chemistry , catalysis , computer science , operating system
The [2+2] photocycloaddition of allenes 15 – 18 , 23 and 26 was studied. Irradiation of a solution of these substrates in acetonitrile at 300 nm resulted in the clean conversion of the starting materials into a mixture of photoproducts. The major product in all cases was a bicyclic pyrrole or furan fused to an eight membered ring (43–70 % yield). The formation of these products is thought to be a result of a heteroatom‐induced fragmentation of the straight adduct ( 7 ). This is supported by irradiation of the carbon analogue 32 which allowed the isolation of straight adduct 45 after catalytic hydrogenation in 27 %. The minor crossed photoproducts were isolated in 10–20 % yield. The observed major/minor ratio of 4:1 was not affected by the variation of substituents on the cyclohexene ring. Introduction of a substituent on the allene had a more significant effect on the ratio which changed to 2:1.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)