Carbanions. 17. Rearrangements of 2, 2-diphenyl-4-pentenyl alkali metal compounds

E Grovenstein Jr, AB Cottingham

Index: Grovenstein,E.; Cottingham,A.B. Journal of the American Chemical Society, 1977 , vol. 99, p. 1881 - 1889

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Citation Number: 15

Abstract

Abstract: 2, 2-Diphenyl-4-pentenyllithium (2) rearranges in tetrahydrofuran at-50 to 0 “C to give, according to the products of protonation and carbonation, chiefly 1, I-diphenyl-4- pentenyllithium (4)(product of migration of allyl). With 2, 2-diphenyl-4-pentenyl-3-''C-lithium (2*), carbon-14 was found in 4 either at the terminal C-5 position (“inversion” of the allyl group) or scrambled at positions C-3 and C-5; the amount of scrambling increased with ...