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Cycloaddition of Acyclic Conjugated Dienes with a Tetrachloro‐Substituted Oxyallyl Intermediate Generated from Pentachloroacetone
Author(s) -
Föhlisch Baldur,
Korfant Hilmar,
Meining Holger,
Frey Wolfgang
Publication year - 2000
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 - 10.1002/1099-0690(200004)2000:7<1335::aid-ejoc1335>3.0.co;2-2
Subject(s) - chemistry , conjugated system , cycloaddition , medicinal chemistry , sodium , organic chemistry , stereochemistry , catalysis , polymer
Abstract Pentachloroacetone ( 1 ) reacts with several conjugated dienes in the presence of sodium trifluoroethoxide/trifluoroethanol to form cycloadducts of a tetrachlorooxyallyl intermediate 6 , mainly in the [4+3] mode. Representative [4+3] cycloadducts, i.e. α,α,α′,α′‐tetrachlorocycloheptenones 9 , have been dehalogenated and dehydrohalogenated, furnishing α,α′‐dichlorotropones 15 in high yields.