ISSN:
0009-2940
Keywords:
Cyclophanes
;
Benzenopyrenophane, 4,9-bridged
;
Sulfones, pyrolysis of
;
Photodesulfurization
;
[2]Naphthaleno[2]paracyclophane, 1,5-bridged
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
2,11-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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931261126
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