Abstract
Abstract2,11‐Dithia[3]metacyclo‐ (14b) and 2,11‐dithia[3]paracyclo[3]‐(4,9)pyrenophane (14c) were obtained by the coupling reactions of 4,9‐bis(chloromethyl)pyrene (12) with the corresponding bis(mercaptomethyl)benzenes (13b, c). Attempted pyrolysis of the disulfones 18b, 18c to afford [2]metacyclo‐ (19b) and [2]paracyclo[2](4,9)pyrenophane (19c) failed. Only the ring cleavage products 16 and 20 were obtained. The sulfur dioxide extrusion by vapor‐phase pyrolysis of the corresponding disulfone 18 to the highly strained 19 clearly demonstrates the limits of these preparative ring contraction method. The photolytic desulfurization of 14c afforded the [2](1,5)naphthal‐eno[2]paracyclophane analogue 21 instead of [2]paracyclo[1]‐(4,9)pyrenophane 21′. The mechanism of the pyrolysis and photolysis reactions is discussed.
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