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The hydrolysis of α,α'‐dimethoxydihydrofurans
Author(s) -
Hirsch Jerry A.,
Szur Alex J.
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090310
Subject(s) - chemistry , hydrolysis , stereospecificity , hydrazine (antidepressant) , isomerization , hydrate , conjugated system , organic chemistry , combinatorial chemistry , chromatography , catalysis , polymer
A series of α,α ‐dimethoxydihydrofurans have been prepared and subjected to various acidic and neutral hydrolysis conditions in attempts to prepare conjugated enediones in a stereospecific manner. Isomerization of the 3‐hexene‐2,5‐diones and rearrangements of other enediones to β,γ‐unsaturated‐γ‐lactones have been uncovered. Methods of assignment of stereochemical configuration to the enediones are evaluated; reaction with hydrazine hydrate in the absence of acid is proposed as a useful criterion.