The Journal of Organic Chemistry

SN2 displacements and reductive coupling of ketones with olefins in N, N-diethylacetamide and N-ethylpyrrolidone

AF Sowinski, GM Whitesides

Index: Sowinski,A.F.; Whitesides,G.M. Journal of Organic Chemistry, 1979 , vol. 44, # 14 p. 2369 - 2376

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Citation Number: 61

Abstract

N, N-Diethylacetamide (DEA) and N-ethylpyrrolidone (NEP) are complementary to hexamethylphosphoric triamide (HMPA), dimethylformamide, and dimethyl sulfoxide as solvents in which to carry out several reactions commonly conducted in polar, aprotic media. Reaction of neopentyl tosylates with lithium halides in DEA and NEP gives good yields of neopentyl halides. Ketones and terminal olefins are reductively coupled to tertiary ...