Abstract
Irradiation (λ > 300 nm) of 1-naphthyldiazomethane (11) or 1-naphthyldiazirine (12) isolated in an argon matrix at 10 K produces 4,5-benzobicyclo[4.1.0]hepta-2,4,6-triene (2) and a small amount of triplet 1-naphthylcarbene (1). Cyclopropene 2 is characterized by infrared and UV/visible spectroscopy while triplet 1-naphthylcarbene (1) is characterized by infrared, UV/visible, and ESR spectroscopy. Experimental and computed (B3LYP/6-31G*) IR spectra display good agreement. Carbene 1 and cyclopropene 2 are thermally stable in the matrix at 10 K, although they may be interconverted photochemically. Further irradiation of the matrix under a number of conditions (λ > 300, λ = 342 ± 10, λ > 497, or λ = 544 ± 10 nm) causes disappearance of carbene 1 and exclusive growth of cyclopropene 2. Shorter wavelength photolysis (λ = 290 ± 10 nm) triggers reversion of 2 back to 1. Conversion of either compound to 4,5-benzocyclohepta-1,2,4,6-tetraene (6), 2-naphthylcarbene (8), or 2,3-benzobicyclo-[4.1.0]hepta-2,4,6-triene (...
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