title: A m-benzyne to o-benzyne conversion through a 1,2-shift of a phenyl group.
abstract: Pyrolysis of two differently labeled versions of 3-phenylphthalic anhydride shows that a m-benzyne can form the related o-benzyne through shift of a phenyl group. The highest energy point in the process is the transition structure for a reverse carbon-hydrogen insertion in an intermediate benzopentalene. With the minor addition of an intermediate alkyne formed through a Roger Brown rearrangement, the original mechanism for formation of acenaphthalene accommodates the labeling results.
authors.affiliation: Contribution from the Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Michael E
authors.initials: ME
authors.lastname: Blake
authors.forename: Kevin L
authors.initials: KL
authors.lastname: Bartlett
authors.forename: Maitland
authors.initials: M
authors.lastname: Jones