Molecules with Twist Bent Bonds. The Synthesis, Properties, and Reactions of trans-Bicyclohept-3-ene and Certain Methylated Derivatives

Article abstract of DOI:10.1021/ja00189a046

trans-Bicyclo<4.1.0>hept-3-ene, 7-methyl-trans-bicyclo<4.1.0>hept-3-ene, and 7,7-dimethyl-trans-bicyclo<4.1.0>hept-3-ene have been synthesized.Comparison of their ease of oxidation with the ease of oxidation of the analogous cis-bicyclo<4.1.0>hept-3-enes has been made.Both the thermal and transition-metal complex promoted rearrangements of the trans-bicyclo<4.1.0>hept-3-enes have been studied.These systems thermally convert to the cis-bicyclo<4.1.0>hept-3-enes above 100 deg C and are catalytically rearranged at ambient temperature.Trans to cis isomerization alsooccurs at ambient temperature under photoinduced single electron transfer conditions.