Access to the naphthylcarbene rearrangement manifold via isomeric benzodiazocycloheptatrienes

PA Bonvallet, EM Todd, YS Kim…

Index: Bonvallet, Paul A.; Todd, Eric M.; Kim, Yong Seol; McMahon, Robert J. Journal of Organic Chemistry, 2002 , vol. 67, # 25 p. 9031 - 9042

Full Text: HTML

Citation Number: 15

Abstract

Irradiation (λ= 670 or> 613 nm) of 4, 5-benzodiazocycloheptatriene (15), matrix isolated in argon at 10 K, produces primarily 2, 3-benzobicyclo [4.1. 0] hepta-2, 4, 6-triene (9) accompanied by small amounts of triplet 4, 5-benzocycloheptatrienylidene (2) and 2- naphthylcarbene (10). A reversible photoequilibrium is established in which 9 is converted to 10 at λ= 290 nm and then regenerated at λ= 360 nm. Similarly, matrix-isolated 2, 3- ...