Phosphanalkylene, 53. Synthese von α,β1-ungesättigten Cycloalkanonen aus Bis[(1-acylalkyliden)1-triphenylphosphoranen] – Eine Methode zur Überführung von Carbonsäure-Anhydriden in carbocyclische und heterocyclische Verbindungen
✍ Scribed by Bestmann, Hans Jürgen ;Pichl, Rainer ;Zimmermann, Reiner
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 1993
- Tongue
- English
- Weight
- 568 KB
- Volume
- 126
- Category
- Article
- ISSN
- 0009-2940
No coin nor oath required. For personal study only.
✦ Synopsis
Phosphonium ylides / Wittig reactions, intramolecular / Aldol condensations, intramolecular / 2-Cycloalken-1 -ones / 2-Cycloalkene-l,4-diones Phosphane Alkylenes, 53[11. -Synthesis of a$-Unsaturated Cycloalkanones from Bis[(l-acylalky1idene)triphenylphosphoranes] -A Method for the Transformation of Acid Anhydrides into Carbocyclic and Heterocyclic Compounds* Alkaline hydrolysis of bis[( 1-acylalky1idene)triphenylphos-group in the a-position. The reactions of 3 with aldehydes phoranes] 3 leads to 2-cycloalken-1-ones 6. Intramolecular (molar ratio 1 : 1) lead to the formation of mono Wittig com-Wittig reaction of an intermediately formed monoacyl ylide 4 pounds 15 which can cyclize affording 5-and 6-membered 3and intramolecular aldol condensation of a diketone 5, resultalkenyl-2-cycloalken-1-ones 16. Since the ylides 3 are easily ing from hydrolysis of both ylide functions, are discussed available from acid anhydrides the reaction sequences repas possible reaction mechanisms. The oxidation of 3 with resent versatile approaches for the transformation of acid an-Hz02. Ph3P0 yields 7-and 8-membered 2-cycloalkene-1,4-hydrides into 2-cycloalken-1-ones. diones 12, presumely via mono ylides 11 carrying an aldehyde