Open AccessGas-phase pyrolytic formation and dimerization of benzocyclobutenes: Synthesis of [2 4 ](1,2,4,5) cyclophane
Author(s) -
Bruce E. Eaton,
Evan D. Laganis,
V. Boekelheide
Publication year - 1981
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.78.11.6564
Subject(s) - cyclophane , pyrolytic carbon , pyrolysis , chemistry , derivative (finance) , phase (matter) , gas phase , nitrogen , crystal structure , stereochemistry , crystallography , organic chemistry , financial economics , economics
Gas-phase pyrolysis of benzocyclobutenes in a nitrogen stream at 450°C is a convenient efficient method for preparing dibenzocyclooctadienes. Application of this method to benzo[1,2;4,5]dicyclobutene gives [24 ](1,2,4,5)cyclophane directly. However, under the same reaction conditions, 3,6-dimethylbenzo[1,2;4,5]dicyclobutene gives the open [2.2]orthocyclophane derivative, whose structure has been established by x-ray crystallographic analysis of the corresponding iron complex.