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Electrophilic carboxylation of alkenes
Author(s) -
Mayr Herbert,
Von Der Brüggen Uwe
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210221
Subject(s) - chemistry , boron trichloride , electrophile , carboxylation , medicinal chemistry , potassium , boron , electrophilic addition , organic chemistry , catalysis
In the presence of 1.2 equivalents of boron trichloride 2,2‐dichloro‐1,3‐benzodioxol ( 2 ) reacts with alkenes 4 to form 1:1 addition products 6 , which are converted into the unsaturated tert ‐butyl esters 7 on treatment with potassium tert ‐butoxide. In the presence of ZnCl 2 , these reactions do not usually terminate at the 1:1‐product stage, and 2,2‐disubstituted 1,3‐benzodioxols 5 are formed by reaction of 2 with two equivalents of 4a – f .