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Reversible Umlagerung eines cis ‐2‐Vinyl‐cyclopropylformaldehydes zu einem Dihydrooxepin. Vorläufige Mitteilung
Author(s) -
Rey Max,
Dreiding André S.
Publication year - 1965
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19650480819
Subject(s) - chemistry , aldehyde , adduct , tetracyanoethylene , enol , enol ether , cycloaddition , stereochemistry , bicyclic molecule , double bond , vinyl ether , medicinal chemistry , formaldehyde , polymer chemistry , organic chemistry , catalysis , polymer , copolymer
Evidence is given for a fast reversible 2‐vinylcyclopropylformaldehyde‐dihydro‐oxepine rearrangement. Bicyclo[3.1.0]hex‐2‐ene‐6‐endo‐formaldehyde and 2‐oxa‐bicylo[3.2.1]octa‐3,6‐diene coexist in a 7:3 equilibrium, which is pulled in the direction of the enol ether by a cycloaddition with tetracyanoethylene, and in the direction of the aldehyde by interaction with LiAlH 4 , Ag 2 O or NaHSO 3 . Decomposition of the pure hydrogensulfite adduct of the aldehyde refurnishes the 7:3 mixture.
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