Adduct of iodonium ylide with sulfur trioxide and its reaction with olefins

Journal Article · Tue Sep 20 04:00:00 EDT 1988 · Journal of Organic Chemistry of the USSR (English Translation); (USA)

OSTI ID:5373438

Semerikov, V N; Sorokin, V D; Zhdankin, V V; Koz'min, A S; Zefirov, N S ^[1]

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1. M.V. Lomonosov Moscow State Univ. (USSR)

In a continuation of researches into the sulfonate activation of electrophilic reagents the authors have studied the reaction of sulfur trioxide with (phenyliodonio)dimethyloxycarbonylmethanide (I). This reaction takes place exothermically when equimolar amounts of the ylide (I) and sulfur trioxide are mixed in anhydrous methylene chloride at {minus}78{degree}C. It gives a quantitative yield of ((bis-methoxycarbonyl)) phenyliodoniomethanesulfonate (II). Compound (II) is unstable at room temperature and decomposes after a few hours with the formation of iodobenzene and diathene. The products from decomposition of the reagent (II), including tetramethoxycarbonylethene and the dithiane, were formed in the reactions of (II) with olefins, and iodobenzene was realized. The authors have obtained for the first time a relatively stable adduct of an iodonium ylide with such a Lewis acid as sulfur trioxide.

• OSTI ID: 5373438
• Journal Information: Journal of Organic Chemistry of the USSR (English Translation); (USA), Journal Name: Journal of Organic Chemistry of the USSR (English Translation); (USA) Vol. 24:4; ISSN 0022-3271; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ADDUCTS
AROMATICS
CHALCOGENIDES
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
INFRARED SPECTRA
IODINATED ALIPHATIC HYDROCARBONS
IODINATED AROMATIC HYDROCARBONS
KINETICS
METHYLENE CHLORIDE
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
REACTION KINETICS
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
SULFUR COMPOUNDS
SULFUR OXIDES
SULFUR TRIOXIDE
YIELDS