Strained aromatic systems. Synthesis of dicyclobuta [1, 2: 3, 4] naphthalenes, dicyclobuta [1, 2: 3, 4] anthracene, and tricyclobutabenzene

…, PJ Garratt, H Shahriari-Zavareh, R Zahler

Index: Doecke, Christopher W.; Garratt, Peter J.; Shahriari-Zavareh, Hooshang; Zahler, Robert Journal of Organic Chemistry, 1984 , vol. 49, # 8 p. 1412 - 1417

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Citation Number: 14

Abstract

The syntheses of tricyclobuta [1, 2: 3, 46, 7] naphthalene (la), dicyclobuta [1, 2: 3, 4] cyclopenta [6, 7] naphthalene (lb), and dicyclobuta [1, 2: 3, 4] cyclohexa [6, 7] naphthalene (IC) are described via a route involving annelation of the appropriate dilithiated 1, 2-diester with 5, 6-bis (bromomethyl) dicyclobutabenzene (6b). The 13C NMR spectra of this series of annelated naphthalenes indicate a considerable change in hybridization at the C-5 (8) ...