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Synthesis of β,γ‐unsaturated phenyl esters by aluminium chloride initiated reactions of allylsilanes with aryl chloroformates
Author(s) -
Mayr Herbert,
Gabriel Andreas O.,
Schumacher Ralf
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199509220
Subject(s) - chemistry , allylic rearrangement , aluminium , trimethylsilane , aryl , yield (engineering) , chloride , aluminium chloride , medicinal chemistry , organic chemistry , ethyl chloroformate , chloroformate , catalysis , alkyl , materials science , metallurgy
Phenyl chloroformate ( 1 ) reacts with the allylsilanes 2a–h in the presence of aluminium chloride to give the β,γ‐unsaturated phenyl esters 3a–h in 50–90% yield. While these reactions proceed in the usual manner with allylic inversion, (1,1‐dimethylallyl)trimethylsilane ( 2i ) reacts with allyl retention to yield the 2,2‐dimethyl‐3‐butenoate 3i . Attempts to use 1 for the phenoxycarbonylation of arenes were not successful.