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Novel Structures from Tris(benzocyclobutadieno)cyclohexatriene: Triscyclopropanation and Trisoxacyclopropanation to the First [2.1.2.1.2.1]Hexaannulanes
Author(s) -
Mohler Debra L.,
Vollhardt K. Peter C.,
Wolff Stefan
Publication year - 1995
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.199505631
Subject(s) - tris , cyclopropanation , trimethylsilyl , decomposition , derivative (finance) , chemistry , medicinal chemistry , polymer chemistry , organic chemistry , catalysis , biochemistry , financial economics , economics
Surprisingly thermally stable , the hexaannulanes 1 can be heated without decomposition to 200 °C ( 1a ) or 180 °C ( 1b ). They are accessible in good yields from tris(benzocyclobutadieno)cyclohexatriene by cyclopropanation with Et 2 Zn or by epoxidation with 3,3‐dimethyl‐1,2‐dioxacyclopropane, respectively, and were characterized by spectroscopy and X‐ray crystallography in the case of 1a for a hexakis(trimethylsilyl) derivative.