A facile synthesis of 1,5-dienes by a regioselective allylation of the allylic carbanions generated from allyl phenyl selenides
About: This article is published in Chemical & Pharmaceutical Bulletin.The article was published on 1992-01-25 and is currently open access. It has received 3 citations till now. The article focuses on the topics: Allylic rearrangement & Coupling reaction.
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TL;DR: In this paper , the authors summarized the developments and advancements of allyl-(aza)allyl coupling reactions in the past years and organized them according to the transition metals used in allyl-allyl couplings including their own work.
Abstract: We have summarized the developments and advancements of allyl-(aza)allyl coupling reactions in the past years. Since the first report in 1980, Pd-catalyzed allyl-allyl couplings have not drawn chemists' much attention for almost 20 years. Not until the last two decades, transition-metal-catalyzed allyl-(aza)allyl transformations have been retrieved vital interest and significantly developed in many respects, including metal-catalyst, ligand development, mechanistic understanding, substrate scope, and applications in the preparation of complex functional molecules. This review is organized according to the transition metals used in allyl-allyl coupling reactions including our own work. Besides, transition-metal-free, allyl-azaallyl cross-couplings and applications in the total synthesis of natural products and drugs have also been included.
2 citations
15 Apr 2001
TL;DR: The 2-propenylseleno)benzene (2-Propenylenide) is an organoselenium compound that is stable indefinitely in the freezer, but will slowly turn yellow at room temperature and in ambient light due to the formation of diphenyl diselenide.
Abstract: [14370-82-2] C9H10Se (MW 197.14)
InChI = 1S/C9H10Se/c1-2-8-10-9-6-4-3-5-7-9/h2-7H,1,8H2
InChIKey = HGVAUOKQFBXKDV-UHFFFAOYSA-N
(metalated derivatives are ambident nucleophiles;2,4,6-9,11,15 sigmatropic rearrangements produce allyl alcohols and amines;9-12 cleavage of SeC bond provides a source of allyl anions,13 cations,6,14,15 and radicals16,17)
Alternate Name: (2-propenylseleno)benzene.
Physical Data: bp 65–68 °C/1 mmHg;2 82–83 °C/3 mmHg.3
Solubility: insol water; sol most organic solvents.
Preparative Methods: from Allyl Bromide,2, 4 chloride, or mesylate4 and sodium benzeneselenolate (prepared by reduction of Diphenyl Diselenide,2, 4 or deprotonation of Benzeneselenol).3 Numerous other procedures have been used, including the reaction of allylsilanes with Benzeneselenenyl Chloride,5 allyl acetates with Phenyl Trimethylsilyl Selenide,5 allyl halides with PhSeTl,5 and allylamines with PhSeLi (Ru catalyzed).5
Purification: distillation in vacuo2, 3 or chromatography on silica gel4 before use.
Handling, Storage, and Precautions: the compound is stable indefinitely in the freezer, but will slowly turn yellow at room temperature and in ambient light due to the formation of diphenyl diselenide. The compound is not excessively malodorous when pure, but should be prepared and handled in a fume hood due to the toxic nature of many organoselenium compounds.