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A p ‐benzyne to m ‐benzyne conversion through a 1,2‐shift of a phenyl group. Completion of the benzyne cascade
Author(s) -
Polishchuk Alexei L.,
Bartlett Kevin L.,
Friedman Lee A.,
Jones Maitland
Publication year - 2004
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.797
Subject(s) - aryne , triphenylene , chemistry , medicinal chemistry , group (periodic table) , pyrolysis , stereochemistry , computational chemistry , organic chemistry , molecule
Abstract Pyrolysis of 1,6‐diphenylhexa‐1,5‐diyne‐ cis ‐3‐ene at 800–1000°C leads to a mixture of 1‐ and 2‐phenylbiphenylene, along with triphenylene. Formation of the two biphenylenes is taken as strong evidence of the rearrangement of a p ‐benzyne into a m ‐benzyne through a shift of one of the phenyl groups. Copyright © 2004 John Wiley & Sons, Ltd.