Influence of the heterocyclic side ring on orientation during nitrations of 1, 2??alkylenedioxy??annelated benzenes and their mononitro derivatives

IM Takakis, PM Hadjimihalakis

Index: Takakis, Ioannis M.; Hadjimihalakis, Phaedon M. Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 3 p. 625 - 634

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Citation Number: 4

Abstract

Abstract Nitration of 1, 2-alkylenedioxybenzenes 1 furnished the respective nitro derivatives 3 and 4 in the relative ratios: 4a: 3a/100: trace, 4b: 3b/98: 2.4, 4c: 3c/86: 14, 4e: 3e/91: 9 and 4f: 3f/99: 1.3. Nitration of 4 gave 5a: 6a: 8a/0: 0: 100, 5b: 6b: 8b/7.7: 3.2: 89, 5c: 6c: 8c/23: 12: 65, 5d: 6d: 8d/14: 74: 12, 5e: 6e: 8e/27: 18: 55 and 5f: 6f: 8f/23: 7.0: 70. Nitration of the isomeric 3 afforded the dinitro products 5, 6 and 7 in the following relative ratios: 5a: 6a: ...