On the reaction of trisubstituted olefins with phenylselenenyl chloride in methanol
โ Scribed by P. Ceccherelli; M. Curini; M.C. Marcotullio; O. Rosati
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 474 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
The interaction of trisubstituted olefins with excess phenylselenenyl chloride in methanol generates chloromethoxy and dimethoxyderivatives. The mechanism of this transformation has been investigated.
Phenylselenenyl chloride is known to react with olefins to produce, in an anti-stereospecific fashion, the /?-chloro-,l fl-hydroxy-,' or ,!&methoxy-selenides3 depending on the reaction conditions. The removal of the selenium containing moiety from these adducts can be achieved, inter
๐ SIMILAR VOLUMES
Allenoxyborinates, easily generated via the 1,4-addition of dicyclohexylborane to a,~acetylenic ketones, react in situ with excess starting ketone to afford stereodefined, functionalized trisubstituted olefins in high yields.
In continuation of the studies on synthetic applications of trialkyl-l-alkynylborates (I), " 2 the present paper discloses a novel reaction of I with oxiranes II affording non-isolable intermediates III, from which we have obtained r-hydroxyketones V, trisubstituted olefins VI, and a tetrasubstitute
The Reaction of ฮฑ,ฮฒ-Acetylenic Ketones with Dicyclohexylborane: Stereoselective Synthesis of Functionalized Trisubstituted Olefins. -ฮฑ,ฮฒ-Acetylenic ketones (I) (6 compounds) undergo 1,4-addition of dicyclohexylborane to give allenoxyborinate intermediates which react with excess starting ketone to