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Effects of hexamethylphosphoric triamide (hempa) upon allylic grignard reagents: Synthesis of long chain alkenol acetates
Author(s) -
Sonnet P. E.,
Bierl B. A.,
Beroza M.
Publication year - 1974
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02632387
Subject(s) - allylic rearrangement , reagent , chemistry , alkene , protonation , tetrahydrofuran , medicinal chemistry , halide , double bond , group 2 organometallic chemistry , grignard reaction , organic chemistry , stereochemistry , molecule , catalysis , ion , solvent
Abstract E or Z allylic Grignard reagents reacted with allylic halides in tetrahydrofuran‐Hempa to give products in which the double bond from the organometallic fragment was predominantly Z. Protonation of the allylic Grignard reagents gave an increased proportion of Δ2‐alkene and a higher ratio of Z:E isomers when Hempa was added.