Synthesis of anti-4,5,14,15-Tetramethyl2>(2,7)naphthalenophane-1,11-diene and its Dianion. ESR and ENDOR Studies of its Radical Anion and Other Related Radical Ions

Article abstract of DOI:10.1021/jo00196a005

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.