Synthesis of β,γ‐unsaturated phenyl esters by aluminium chloride initiated reactions of allylsilanes with aryl chloroformates | Zendy

Mayr Herbert | Zendy; Gabriel Andreas O. | Zendy; Schumacher Ralf | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research