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Regiochemistry of the Intramolecular [2 + 2]‐Photocycloaddition of Cyclohexenone to Vinyl Ethers
Author(s) -
Fischer Evelyn,
Gleiter Rolf
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198909251
Subject(s) - regioselectivity , methylene , intramolecular force , chemistry , vinyl ether , polarization (electrochemistry) , cyclohexenone , ether , double bond , medicinal chemistry , photochemistry , stereochemistry , polymer chemistry , organic chemistry , catalysis , polymer , copolymer
What influence have chain length and polarization of the vinyl ether double bond on the title reaction? This problem has been studied with the compounds 1–3 . With chains of three and four methylene groups, the different polarization only influences the quantum yield; exclusively head‐to‐head products are formed. With two methylene groups, the polarization also influences the regiochemistry.