Journal of Organic Chemistry p. 4128 - 4132 (1984)
Update date:2022-08-16
Topics:
Rohrbach, William D.
Gerson, Fabian
Moeckel, Reinhart
Boekelheide, Virgil
A synthesis of anti-4,5,14,15-tetramethyl<22>(2,7)naphthalenophane-1,11-diene (4) has been achived in ten steps from 1,8-naphthalic anhydride in an overall yield of 4percent.The key step in the synthesis employed a double-barreled sulfur analogue of the Sommelet-Hauser rearrangement.Unexpectedly, formation of the dianion and radical anion of 4 occured without intramolecular cyclization.The radical anions and the radical cations both of 4 and of anti-4,5,14,15-tetramethyl<22>(2,7)naphthalenophane (19) have been characterized by ESR and ENDOR spectroscopy.
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