… of dilithiated vicinal diesters and dilithiated 1, 2-dicarboximides with methyl iodide,. alpha.,. omega.-dihalides,. alpha.,. omega.-ditosylates and. omega.-bromo esters

KG Bilyard, PJ Garratt, R Hunter…

Index: Bilyard, Kevin G.; Garratt, Peter J.; Hunter, Roger; Lete, Ester Journal of Organic Chemistry, 1982 , vol. 47, # 24 p. 4731 - 4736

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Citation Number: 31

Abstract

-7 c, R= C, H, dilithiated nature of 1 la is substantiated by its chemical reactions and by its 13C NMR spectrum. Reaction of 1 la with methyl iodide gave the dimethylated derivative 12a in 90% isolated yield. The 13C NMR spectrum of 1 la in hexamethylphosphoric triamide (HMPA) showed signals at 156.7, 70.0, 54.0, 39.3, 31.7, and 30.7 ppm, assigned respectively to C-1, C-2,(3-5, C-3, C-4, and C-6, consistent with a symmetrical dilithiated ...