Photochemical transformations of small ring compounds. XLI. Orbital symmetry and steric control in the photorearrangement of 1, 3, 5-hexatrienes to bicyclo [3.1. 0] …

A Padwa, L Brodsky, S Clough

Index: Padwa,A. et al. Journal of the American Chemical Society, 1972 , vol. 94, # 19 p. 6767 - 6775

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Abstract

Abstract: Irradiation of (Z, Z, E)-or (Z, Z,. Z)-l, 2, 6-triphenylhexa-l, 3, 5-triene (6 or 13, respectively) gave rise to 4-exo, 6-exo-(8) and 4-exo, 6-endo-3, 4, 6-triphenylbicyclo [3.1. O] hex-2-ene (17), respectively. The formation of bicyclohexenes 8 and 17 from the (Z, Z, E)- and (Z, Z, Z)-trienes was shown to be a two-photon reaction involving initial cis-trans isomerization about the terminal C1-C2 bond followed by, 4,+* 2. cycloaddition. Irradiation ...