Abstract
Abstract7‐Adamantylidene‐1,3,5‐cycloheptatriene (18) was prepared via thermolysis of the thietane 22, produced in the cycloaddition of 2‐adamantanethione with 8‐oxoheptafulvene (1). The latter reaction also afforded the thiophene 23, presumably via [8 + 2]‐cycloaddition. Reaction of singlet oxygen (1O2) with heptafulvene 18 gave the [4 + 2]‐tropilidene endoperoxide 24, while 4‐methyl‐4H‐1,2,4‐triazole‐3,5‐dione (MTAD) led to the [8 + 2]‐urazole 26. Singlet oxygenation of thietane 22 produced the [4 + 2]‐tropilidene endoperoxide 27, but with MTAD the strained [4 + 2]‐norcaradiene urazole 28 was obtained. The thiophene 23 gave with 1O2 and MTAD the [4 + 2]‐norcaradiene products 29 and 30, respectively. X‐ray analysis confirmed the urazole 30 structure.
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