Synthesis of anti-4, 5, 14, 15-tetramethyl [22](2, 7) naphthalenophane-1, 11-diene and its dianion. ESR and ENDOR studies of its radical anion and other related …

…, F Gerson, R Moeckel, V Boekelheide

Index: Rohrbach, William D.; Gerson, Fabian; Moeckel, Reinhart; Boekelheide, Virgil Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4128 - 4132

Full Text: HTML

Citation Number: 13

Abstract

A synthesis of anti-4, 5, 14, 15-tetramethyl [22](2, 7) naphthalenophane-l, ll-diene (4) has been achieved in ten steps from 1, 8-naphthalic anhydride in an overall yield of 4%. 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 occurred without intramolecular cyclization. The radical anions and the radical cations both of 4 and ...