[English name] vinyltriphenylphosphinium bromide
[Formula] c20h18brp
[molecular weight] 369.23
[Ca login No.] [5044-52-0]
[physical properties] the reagent is white powder, MP 189 ~ 190 OC, soluble in TERT butanol.
[preparation and commercial] the reagent can be prepared by reacting 2-chloroethyl triphenylphosphonium bromide with triethylamine (72%) or 2-phenoxyethyl triphenylphosphonium bromide with boiling ethyl acetate (92%). Large multinational reagent companies have sales of vinyl triphenylphosphonium bromide.
[note] it has hygroscopic property, irritant to human body, and can cause sneezing and other symptoms. The reaction should be carried out in the fume hood.
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The formation of alkylphosphonium salt can react with a lot of nucleophiles such as alcohol, primary or secondary amine (formula 1) [1], mercaptan, carboxylic acid (formula 2) [2] and carbonanions with nucleophile ability [3] to form alkylphosphonium salt by the reaction of three phenylphosphonium salts with vinyl bromide.
Vinyl triphenylphosphonium brominated with aldehydes can react with aldehydes to form alkene [1] (formula 3), copper salt as catalyst has a high yield [4] (formula 4), the reaction product is mostly CIS, adding 5 equivalent hexamethylphosphoryltriamide can improve its cis yield, which is also known as schweizwer reaction. The secondary amines, pyrrole, sulfamoyl, phosphobenzoimide and their salts react with vinyltriphenylphosphonium bromide to form enamine. The CIS structure is the main product.
The synthesis of cyclic compounds schweizwer reaction is mainly used to synthesize cyclic or heterocyclic compounds (formula 5-8) [5-8].
reference
1. Andrés, J. I.; Alcázar, J.; Alonso, J. M.; Alvarez, R. M.; Cid, J. M.; De Lucas, A. I.; Fernández, J.; Martínez, S.; Nieto, C.; Pastor, J.; Bakker, M. H.; Biesmans, I.; Heylen, L. I.; Megens, A. A. Bioorg. Med. Chem. Lett., 2003, 13, 2719.
2. Karatholuvhu, M. S.; Fuchs, P. L. J. Am. Chem. Soc., 2004, 126, 14314.
3. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron, 1995, 51, 9985.
4. Shen, Y.; Yao, J. J. Org. Chem., 1996, 61, 8659.
5. Déziel, R.; Malenfant, E.; Thibault, C.; Fréchette, S.; Gravel, M. Tetrahedron Lett., 1997, 38, 4753.
6. Jones, G. B.; Guzel, M.; Mathews, J. E. Tetrahedron Lett., 2000, 41, 1123.
7. Clerici, F.; Gelmi, M. L.; Trimarco, P. Tetrahedron, 1998, 54, 5763.
8. Kumarn, S.; Shaw, D. M.; Longbottom, D. A.; Ley, S. V. Org. Lett., 2005, 7, 4189.
This paper is from: modern organic synthetic reagents -- properties, preparation and reaction, edited by Hu Yuefei, et al
Related reaction
Common pyrrole synthesis reactions