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Abstract
Ultraviolet irradiation of (Z)-2,9-bismethylene-13-thiabicyclo[8.2.1]-5-tridecene (8), prepared from (Z)-2,9-dichloro-13-thiabicyclo[8.2.1]-5-tridecene (1) by way of (Z)-2,9-dioxo-13-thiabicyclo[8.2.1]-5-tridecene (7), affords (Z)-3,10-bismethylene-1,6,11-dodecatriene (15) in trimethylphosphite and a 9:1 mixture of (Z)-2-methylenebicyclo[7.3.1]trideca-5(6),9(10)-diene (16) and (Z,Z,Z)-bicyclo[6.4.2]tetradeca-1(12),4(5),8(9)-triene (17) when irradiated in hexane. Similarly photolysis of 2,5-bis(3-methyl-1-buten-2-yl)thiolane (18) in hexane affords 2-isopropyl-4-(3-methyl-1-buten-2-yl)-cyclohexene (19). Mechanisms involving radicals are proposed.