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PHOTOCHEMISTRY OF CONJUGATED POLYACETYLENES: [2+2] PHOTOCYCLOADDITION OF l‐PHENYL‐l,3,5‐HEXATRIYNES WITH SOME OLEFINS
Author(s) -
Chung Chang Beom,
Kwon Jang Hyuk,
Shim Sang Chul,
Hoshino Mikio
Publication year - 1993
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1993.tb09542.x
Subject(s) - chemistry , regioselectivity , acrylonitrile , photochemistry , methylene , excited state , conjugated system , styrene , nucleophile , medicinal chemistry , organic chemistry , catalysis , copolymer , physics , nuclear physics , polymer
— Irradiation of 1‐phenyl‐1,3,5‐hexatriynes with various olefins in methylene chloride yields [2 + 2] type 1:1 photoadducts. The photoreaction proceeds through a triplet excited state and shows site selectivity and regioselectivity. Olefins with electron‐withdrawing substituents, such as dimethyl fumarate, fumaronitrile, acrylonitrile, methyl acrylatc, and styrene, are more reactive than electron‐rich olefins, suggesting that the triplet excited states of 1‐phenyl‐1,3,5‐hexatriynes have a nucleophilic radical character.