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Syntheses of Carboxylic Acids from 1, 1‐Dichloroehylene
Author(s) -
Bott K.,
Hellmann H.
Publication year - 1966
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196608701
Subject(s) - carbonium ion , chemistry , electrophile , sulfuric acid , alkyl , organic chemistry , atom (system on chip) , ion , electrophilic substitution , medicinal chemistry , catalysis , computer science , embedded system
Many β‐alkyl‐ and β‐arylpropionic acids are readily obtainable by the reaction of secondary or tertiary alcohols, esters of these, or olefins with the inexpensive 1, 1‐dichloroethylene in sulfuric acid. The success of the synthesis depends on the bulk and energy of the carbonium ion intermediate formed from the alcohols or olefins. With carbonium ions having one H atom attached to the carbonium C atom, electrophilic substitution of the 1,1‐dichloroethylene takes place to a small extent. Dicarboxylic acids and carboxylic acids with higher molecular weights are sometimes formed as a result of side reactions.