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2004•Journal of Physical Organic ChemistryRequires access

A p‐benzyne to m‐benzyne conversion through a 1,2‐shift of a phenyl group. Completion of the benzyne cascade

Alexei L. Polishchuk, Kevin L. Bartlett, Lee A. Friedman, Maitland Jones

Open publisher page 4 citations

Abstract

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.

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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.

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Available abstract

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.

Key concepts: Aryne, Triphenylene, Chemistry, Medicinal chemistry, Group (periodic table), Pyrolysis, Stereochemistry, Computational chemistry

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