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Reversible, thermische Isomerisierung zwischen α, β‐γ, δ‐ungesättigten Aldehyden und Alkenylketenen durch [1,5]‐H‐Verschiebung. Valenzisomerisierung von cis ‐Dienonen, V [1]
Author(s) -
Schiess Peter,
Radimerski Paul
Publication year - 1974
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.19740570834
Subject(s) - chemistry , yield (engineering) , intramolecular force , thermal decomposition , pyrolysis , decomposition , medicinal chemistry , isomerization , torr , chloride , gas phase , phase (matter) , stereochemistry , organic chemistry , catalysis , materials science , physics , metallurgy , thermodynamics
Vapor phase pyrolysis of 2,4‐pentadienaldehyde, of 6‐oxabicyclo[3.1.0]hex‐2‐ene or of 3‐pentenoic acid chloride at 600° (0.1 s/1 Torr) leads to similar mixtures containing the stereoisomers of 2, 4‐pentadienaldehyde and 1‐propenylketene. These compounds, and methyl substituted derivatives thereof, equilibrate at 600° (0.1 s) through intramolecular processes involving cis/trans ‐isomerisations and [1,5]‐H‐shifts. It is shown that α, β‐γ, δ‐unsaturated aldehydes can be prepared in high yield through gas phase thermolysis of appropriately substituted acid chlorides.