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Vinyl Ether–Iron Complexes as Vinyl Cation Equivalents. Preparation and Use of an α‐Acrylic Ester Cation Equivalent
Author(s) -
Chang T. C. T.,
Rosenblum M.
Publication year - 1984
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198400017
Subject(s) - chemistry , cyclohexanone , lithium (medication) , acrylic acid , stereospecificity , ether , methylene , organic chemistry , acetal , vinyl ether , lactone , saponification , catalysis , copolymer , medicine , polymer , endocrinology
The organoiron complex 4 is readily prepared from α‐bromopyruvic ester diethyl acetal, and has been shown to serve as an effective α‐acrylic ester cation equivalent, in the synthesis of α‐methylene‐γ‐lactones. Cyclohexanone lithium enolate is transformed to either the cis or trans fused lactones 12c , t, and ethyl acetoacetate lithium enolate can be converted to the lactone 21 t. The use of methyl 3‐oxohexadecanoate as starting material provides a stereospecific synthesis of protolichesterinic acid methyl ester.