Synthesis and structural study of azidonaphtho-as-triazines." Annelation effect" in azide-tetrazole equilibria

G Hajós, A Messmer, A Neszmelyi…

Index: Hajos, Gy.; Messmer, A.; Neszmelyi, A.; Parakanyi, L. Journal of Organic Chemistry, 1984 , vol. 49, # 17 p. 3199 - 3203

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Citation Number: 17

Abstract

Azide derivatives of the three possible (two angular and one linear) naphtho-as-triazines 7a, loa, and 15a were prepared and the equilibria leading to fused tetrazoles were investigated by NhfR spectroscopy and X-ray analysis. Comparison of the differently annelated systems (topological isomers) revealed an essential" annelation effect": while 3-azidonaphtho [2, 1-c]- m-triazine (7a) and 3-azidonaphtho [1, 2-c]-as-triazine (loa) formed" b-fused" tetrazoles 7b ...