Valenzisomerisierung von  cis ‐Dienonen I. 2‐Vinyl‐3,4,5,6‐tetrahydrobenzaldehyd; Pyrolyse. von 6‐Oxabicyclo [3,1,0] hex‐2‐en [1] | Zendy

Schiess P. | Zendy; Chia H. L. | Zendy

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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.

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