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A Third‐Generation Bicyclopropylidene: Straightforward Preparation of 15,15′‐Bis(hexaspiro[2.0.2.0.0.0.2.0.2.0.1.0]pentadecylidene) and a C 2v ‐Symmetric Branched [15]Triangulane
Author(s) -
von Seebach Malte,
Kozhushkov Sergei I.,
Boese Roland,
BenetBuchholz Jordi,
Yufit Dmitrii S.,
Howard Judith A. K.,
de Meijere Armin
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000717)39:14<2495::aid-anie2495>3.0.co;2-u
Subject(s) - dichlorocarbene , cyclopropane , adduct , chemistry , chloride , copper , medicinal chemistry , stereochemistry , organic chemistry , ring (chemistry)
A new record for spirocyclopropane aggregates is set by the branched triangulane 3 with its fifteen spirofused cyclopropane rings. It is accessible by addition of dichlorocarbene onto the unusual bicyclopropylidene 2 followed by reductive dechlorination. Compound 2 was obtained by conversion of the dibromocarbene adduct of 1 with BuLi in the presence of copper( II ) chloride into the corresponding perspirocyclopropanated bicyclopropylidene and “dimerization” of the dibromocarbene adduct prepared from this compound.