Applications Synthétiques de la Cyclisation d′Alcools Tertiaires γ‐Éthyléniques en α‐Bromotétrahydrofurannes sous l'action du N‐Bromosuccinimide. III. Synthèse du Triméthyl‐2,6,10‐hydroxy‐10‐dodécatriène‐2,6,11‐al ( trans/trans  et  trans/cis ), Hydroxy‐Aldéhyde apparenté aux Sinensals | Zendy

Demole Edouard | Zendy; Enggist Paul | Zendy

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Applications Synthétiques de la Cyclisation d′Alcools Tertiaires γ‐Éthyléniques en α‐Bromotétrahydrofurannes sous l'action du N‐Bromosuccinimide. III. Synthèse du Triméthyl‐2,6,10‐hydroxy‐10‐dodécatriène‐2,6,11‐al ( trans/trans et trans/cis ), Hydroxy‐Aldéhyde apparenté aux Sinensals

Author(s) -

Demole Edouard,

Enggist Paul

Publication year - 1973

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.19730560628

Subject(s) - chemistry , n bromosuccinimide , halogenation , medicinal chemistry , cis–trans isomerism , stereochemistry , organic chemistry

The reaction of 1‐formyl‐ethylidene‐triphenylphosphorane with trans ‐ and cis ‐4,8‐dimethyl‐8‐hydroxy‐deca‐4,9‐dienal ( 7 ) obtained from (±)‐nerolidol through a novel bromination/oxidation/debromination sequence, afforded 2,6,10‐trimethyl‐10‐hydroxy‐dodeca‐2,6‐11‐trienal 6 ( trans‐2/trans ‐6) and 10 ( trans‐2/cis ‐6), respectively. These hydroxyaldehydes closely related to the natural α‐ and β‐sinensals display a powerful, flower‐like odour.

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