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Reaktionen von fulvenen mit 1,3‐dipolaren verbindungen. IV . Umsetzung des 6,6‐diphenylfulvens mit 2,4,6‐triphenylpyrylium‐3‐olat
Author(s) -
Friedrichsen Willy,
Seidel Winfried,
Debaerdemaeker Tony
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200639
Subject(s) - chemistry , sodium borohydride , medicinal chemistry , acetic acid , adduct , reagent , catalysis , organic chemistry
6,6‐Diphenylfulvene (6) reacts with 2,4,6‐triphenylpyrylium‐3‐olate (7) to give three [π2 + π‐4] cyclo‐adducts 8, 9, 10. Reduction of 8 with sodium borohydride yields a cage‐like compound 12 whereas the action of the same reagent on 9 results in the formation of three carbinols 13, 14, 15 . Treatment of 9 with acetic acid/hydrogen chloride yields an isomer 18 . The structures of both 12 and 18 have been established by X‐ray crystallography.