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Halovinylene Carbonates in Organic Synthesis. New synthetic methods (2)
Author(s) -
Scharf HansDieter
Publication year - 1974
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.197405201
Subject(s) - glycolic acid , glyoxylic acid , reagent , chemistry , hydrolysis , organic chemistry , combinatorial chemistry , carbonate , organic synthesis , catalysis , lactic acid , genetics , bacteria , biology
Monohalo‐ and dihalovinylene carbonates constitute a new class of cyclophiles which permit simultaneous introduction of masked α‐hydroxyketo and α‐diketo functions, respectively, into the cycloadducts. Demasking can be performed by simple hydrolysis. Solvolytic opening of the carbonate ring leads to glycolic acid derivatives in the case of the monohalo compounds and to glyoxylic acid derivatives with the dihalo compounds. Preparation of the title compounds, their potential as synthetic reagents, and the chemistry of their simple reaction products are surveyed from a preparative viewpoint.