Synthesis of 4, 4, 9, 17-tetramethyl-2, 6-dithia [7.1] paracyclophane and isolation of atropisomeric forms of the tetraoxide

N Finch, CW Gemenden, BP Korzun

Index: Finch,N. et al. Journal of Organic Chemistry, 1976 , vol. 41, # 15 p. 2509 - 2514

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Citation Number: 3

Abstract

Unsuccessful attempts were made to synthesize a [5. l] metacyclophane by the Stevens rearrangement of the bissulfonium salts derived from the 2, 6-dithia [7. l] metacyclophanes 9, 10, 11, and 12. Compound 15b preferentially underwent a double Sommelet rearrangement in good yield to provide 4, 4, 9, 17-tetramethyl-2, 6-dithia [7. l] paracy-clophane. The bissulfone derived by oxidation was shown to exist in atropisomeric forms 20 and 19. ...