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

doi:10.1002/HLCA.19700530305

Paper

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

Published 1970 · P. Schiess, H. D. Chia

Helvetica Chimica Acta

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53

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Abstract

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-2H-pyran (11) as can be shown by cis-trans-isomerization of the double bond in selectively deuterated 10. The unstable 2H-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.

Study Snapshot

This study presents a method for synthesizing 2-vinyl-3,4,5,6-tetrahydrobenzaldehyde and its equilibration with its valence isomer 4,5-tetramethylene-2H-pyran, and a method for pyrolysis

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

Reactions between Deuterium and Olefins in the Liquid Phase on Platinum Oxide Catalysts

Liquid phase deuterogenation of 1-hexane, DELTA 1,9-, and DELTA 9,10-octalin on platinum oxide catalysts leads to isomerization and formation of deuteriated hexene, with isotopic exchange slow.

Pyrylium Salts Part I. Syntheses

Pyrylium salts are useful intermediates in converting aliphatic materials into aromatic compounds, with potential applications in fluorescent dyes, photosensitizers for silver halides, and photographic emulsions.

The reaction between 2,3-dihydrofuran and dihalocarbenes

2,3-dihydrofuran reacts with dichlorocarbene to produce an adduct, which isomerizes to 2,3-dichloro-5,6-dihydro-2H-pyran, which can be further transformed into aldehyde, bis-dihydr

Reduction of pyrylium salts with sodium borohydride

Sodium borohydride reduces 2,4,6-trialkylpyrylium salts into dienones and lower-boiling products, yielding derivatives of 1,5-diones in acid medium.

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