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Valenzisomerisierung von cis ‐Dienonen I. 2‐Vinyl‐3,4,5,6‐tetrahydrobenzaldehyd; Pyrolyse. von 6‐Oxabicyclo [3,1,0] hex‐2‐en [1]
Author(s) -
Schiess P.,
Chia H. L.
Publication year - 1970
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.19700530305
Subject(s) - chemistry , tetracyanoethylene , isomerization , adduct , yield (engineering) , double bond , medicinal chemistry , pyrolysis , gas phase , valence (chemistry) , organic chemistry , catalysis , thermodynamics , physics
The synthesis of 2‐vinyl‐3,4,5,6‐tetrahydrobenzaldehyde ( 10 ) is described. This compound equilibrates above 70° with its valence isomer 4,5‐tetramethylene‐2 H ‐pyran ( 11 ) as can be shown by cis ‐ trans ‐isomerization of the double bond in selectively deuterated 10 . The unstable 2 H ‐pyran 11 can be trapped as tetracyanoethylene adduct 12 . Gas phase pyrolysis of 6‐oxabicyclo [3.1.0] hex‐2‐ene ( 18 ) at 400°C leads to cis ‐penta‐2, 4‐dienal ( 19 ) in fair yield.