Tetrahedron

1-(Triphenylmethyl) allyl potassium: conformational preference and [1, 2]-rearrangement

E Moret, J Fürrer, M Schlosser

Index: Moret, Etienne; Fuerrer, Juerg; Schlosser, Manfred Tetrahedron, 1988 , vol. 44, # 12 p. 3539 - 3550

Full Text: HTML

Citation Number: 22

Abstract

Upon treatment with the superbasic 1: 1 mixture of butyllithium and potassium tert-butoxide cis-and trans-1, 1, 1-triphenyl-2-butene as well as 4, 4, 4-triphenyl-1-butene undergo a hydrogen/metal exchange to afford 1-(triphenylmethyl) allyl potassium [4, 4, 4-triphenyl-2- butenyl potassium] which can exist in two stereoisomeric forms. Torsional equilibration leads to an endo/exo-ratio of approximately 50: 50. Novel endo-stabilizing interactions are ...