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Synthesis of Centrohexacyclic Hydrocarbons by the Propellane Route: Centrohexaindan and Tribenzocentrohexaquinane
Author(s) -
Kuck Dietmar,
Paisdor Bernd,
Gestmann Detlef
Publication year - 1994
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.199412511
Subject(s) - propellane , ether , diphenyl ether , enol , chemistry , tris , enol ether , organic chemistry , bicyclic molecule , catalysis , biochemistry
Topologically nonplanar hydrocarbons 2 and 3 are available from triptindantrione 1 in only a few steps. Threefold addition of PhLi to 1 and subsequent cyclodehydration provides 2 . In contrast, threefold addition of LiCCR leads surprisingly to a centrohexacyclic tris(enol ether), which can be isomerized thermally into the corresponding triketone.
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