Rh(I)‐katalysierte Umlagerungen von 3,4‐Diacycloxy‐1,5‐hexadiinen; synthese von ( E )‐4‐acyloxymethyliden‐2‐cyclopenten‐1‐onen | Zendy

Pürro Serge | Zendy; Pryde Andrew | Zendy; Zsindely Janos | Zendy; Schmid Hans | Zendy

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Rh(I)‐katalysierte Umlagerungen von 3,4‐Diacycloxy‐1,5‐hexadiinen; synthese von ( E )‐4‐acyloxymethyliden‐2‐cyclopenten‐1‐onen

Author(s) -

Pürro Serge,

Pryde Andrew,

Zsindely Janos,

Schmid Hans

Publication year - 1978

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.19780610124

Subject(s) - chemistry , chloroform , catalysis , medicinal chemistry , stereochemistry , organic chemistry

Rh(I)‐Catalysed Rearrangements of 3,4‐Diacyloxy‐1,5‐hexadiynes; Synthesis of (E)‐4‐Acyloxymethyliden‐2‐cyclopenten‐1‐ones The 3,4‐diacyloxy‐1,5‐hexadiynes 3, 6 and 8 which were synthesized according to a known, slightly modified procedure react with [Rh(CO) 2 Cl] 2 at 100° in chloroform with formation of the ( E )‐4‐acyloxymethyliden‐2‐cyclopenten‐1‐ones 4, 7 and 9 ( Schemes 2, 3 and 4 ), respectively. DL ‐ and meso ‐ 3 as well as trans ‐ and cis ‐ 8 , give the same ( E )‐isomers 4 and 9 , respectively. 3,4‐Diacetoxy‐3, 4‐dimethyl‐1, 6‐diphenyl‐1,5‐hexadiyne ( 10 ) produces with the same catalyst 2,6‐diacetoxy‐3, 4‐dimethyl‐1,6‐diphenylfulvene ( 11 ) (Scheme 5) . A mechanism for the formation of the cyclopentenones is proposed in Scheme 6 .

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