The Photochemical Behavior of Endocyclic Oxa‐enones with Substituents on the CC Double Bond . (Preliminary communication) | Zendy

Margaretha Paul | Zendy

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The Photochemical Behavior of Endocyclic Oxa‐enones with Substituents on the CC Double Bond . (Preliminary communication)

Author(s) -

Margaretha 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.19740570741

Subject(s) - chemistry , isopropyl , double bond , alkyl , enone , bicyclic molecule , carbon atom , deuterium , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , physics , quantum mechanics

Alkyl substituents on C β of the CC double bond hinder both photodimerization of endocyclic oxa‐enones ( 1 – 4 ) and their photocycloaddition to olefins, and they cause a loss of regiospecificity in dimerization in unpolar solvents. The oxa‐enone 3 which like the bicyclic compounds 4 fails to dimerize at all, is shown to incorporate deuterium at the tertiary isopropyl carbon atom in CD 3 OD solution as a consequence of a bimolecularly initiated photoenolization.

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