The Adverse Effect of Benzannelation on the Aromaticity of Oxocinyl Anion: A Combined Experimental and Theoretical Study

HS Kasmai, X Wang, HN Doan, JF Femia…

Index: Kasmai, Hamid S.; Wang, Xiaodong; Doan, Hanh-Nhon; Femia, Josef F.; Yablonsky, Thad M.; Read, Mary E.; Dutton, David T. Helvetica Chimica Acta, 2010 , vol. 93, # 8 p. 1532 - 1544

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Citation Number: 3

Abstract

Abstract A synthesis of 2H-1-benzoxocin from readily available compounds was accomplished. The potentially 'aromatic'π-excessive systems 2H-1-benzoxocinyl and 6H- dibenz [b, f] oxocinyl anions were generated from their corresponding conjugate acid precursors 7c and 8, respectively. It was found that 2H-1-benzoxocinide 3d lacks the type of π-frame stability associated with the parent 2H-oxocinide 1d and that the dibenzo analog ...