Intramolecular reactivity of arylcarbenes: derivatives of o-tolylcarbene

W Kirmse, W Konrad, D Schnitzler

Index: Kirmse, Wolfgang; Konrad, Wolfgang; Schnitzler, Dirk Journal of Organic Chemistry, 1994 , vol. 59, # 14 p. 3821 - 3829

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Citation Number: 17

Abstract

13 14 thermally and photochemically induced 1, Chydrogen shifts in triplet 7 to form singlet o- xylylene (10). Upon short wavelength irradiation, matrix-isolated 10 cyclized to benzocyclobutene (l1). lk It is not clear whether the two-step migration-cyclization mechanism applies at elevated temperatures. Thermolysis of o-tolyldiazomethane (4) produces a different 11: 13 ratio (ca. 3) than the meta and para isomers (ca. 0.8). 12 ...