Chemistry and Applications of Phosphonium and Arsonium Ylides(ⅩⅩⅨ)──Studies on the Hydrolysis of Arsonium Ylides Containing Perfluoroalkyl Group andSynthesis of2-Pyranone Derivatives

Chem. J. Chinese Universities ›› 2002, Vol. 23 ›› Issue (5): 839.

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Chemistry and Applications of Phosphonium and Arsonium Ylides(ⅩⅩⅨ)──Studies on the Hydrolysis of Arsonium Ylides Containing Perfluoroalkyl Group andSynthesis of₂-Pyranone Derivatives

CAO Wei-Guo^1,2, DING Wei-Yu¹, WANG Li-Yan¹, SONG Li-Ping¹, ZHANG Qian-Ying¹

1. Department of Chemistry, Shanghai University, Shanghai 200436 China;
2. Laboratory of Organometallic Chemistry Shanghai Organic Chemistry Institute, Academia Sinica, Shanghai 200032, China

Received:2001-02-05 Online:2002-05-24 Published:2002-05-24

Abstract

Abstract: In the presence of K₂CO₃, reaction of (2-naphthoyl)methyl arsonium bromide (1) with methyl2-perfluoroalkynoates(2) in methylene chloride at room temperature afforded the adduct methyl4-(2-naphthoyl)-2-triphenylarsoranylidene-3-perfluoroalkyl-3-butenoates(3) as major product and 4-(2-naphthoyl)-4-triphenylarsoranylidene-3-perfluoroalkyl-2-butenoat.es (4) as minor product in high yield.Hydrolysis of compound 3 in V(CH₃OH):V(CH₂O) = 9:1 methanolic solution at 80 in a sealed tube,4-perfluoroalkyl-6-(2-naphthyl)-2-pyranones(5) was obtained in an excellent yield.The catalytic hydroly-sis of compound 3 with silica gel and the mechanisms for the formation of the products will also be discuss-ed.

Key words: Arsonium ylide, Hydrolysis, 2-Pyranone derivatives

CLC Number:

O624

TrendMD:

CAO Wei-Guo, DING Wei-Yu, WANG Li-Yan, SONG Li-Ping, ZHANG Qian-Ying. Chemistry and Applications of Phosphonium and Arsonium Ylides(ⅩⅩⅨ)──Studies on the Hydrolysis of Arsonium Ylides Containing Perfluoroalkyl Group andSynthesis of₂-Pyranone Derivatives[J]. Chem. J. Chinese Universities, 2002, 23(5): 839.

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Chemistry and Applications of Phosphonium and Arsonium Ylides(ⅩⅩⅨ)──Studies on the Hydrolysis of Arsonium Ylides Containing Perfluoroalkyl Group andSynthesis of₂-Pyranone Derivatives

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