Trimethylsulfoxonium Iodide Research Articles

Synthesis of thiabenzene oxides and azathiabenzene oxides

AbstractFused thiabenzene oxide, 2‐methyl‐4‐methylthiobenzo[b]thieno[3,2‐c]thiapyran 2,5,5‐trioxide (2) was synthesized by the reaction of 2,3‐dihydro‐2‐bis(methylthio)methylene‐3‐oxobenzo[b]thiophene 1,1‐dioxide (1) with trimethyl sulfoxonium iodide in the presence of sodium hydride in tetahydrofuran. Similarly, fused azathiabenzene oxide, 2‐methyl‐4‐methylthiobenzo[b]thieno[2,3‐c][1,2]thiazine 2,5,5‐trioxide (3) was prepared from 1 and sulfoximine in good yield.

ChemInform Abstract: New Preparations of p‐Nitrophenylcyclopropane.

AbstractThe ylide (II) (prepared in situ from trimethylsulfoxonium iodide and N‐aH) reacts with p‐nitmstyrene (I) to give the title compound (III).

Reaction of 2-bis(methylthio)methyleneindan-1,3-dione with N-ylides and S-ylides.

The reaction of 1 with pyridinium N-ylides (2a, R=H ; 2b, R=3-CH3 ; 2c, R=2-CH3 ; and 2d, R=2-NH2) gave the corresponding stable pyridinium N-allylide compounds (3a and 3b), 2-(2-indanyl) indolizine (4), and 3-(2-indanylidenyl) methylimidazo [1, 2-a] pyridine (5) in good yields. A fused thiabenzene oxide, 2-methyl-4-methylthio-5-oxo-5H-indeno [1, 2-c] thiapyran 2-oxide (8), was synthesized by the reaction of 1 with trimethylsulfoxonium iodide under similar conditions. An azathiabenzene oxide, 2-methyl-4-methylthio-5-oxo-5H-indeno [2, 1-d] [1, 2] thiazine 2-oxide (11), was also synthesized from 2-(1-dimethylsulfoximino-1-methylthio) methyleneindan-1, 3-dione (10), which was prepared from 1 and sulfoximine.

OXIDATION OF THE ALKYL-, ARYL-, AND AMINO-SULFONIUM IONS TO THE SULFOXONIUM IONS AND ITS REACTION MECHANISM

Abstract Hitherto, the preparative method of the sulfoxonium ions has been practically limited to thealkylation of the sulfoxides with methyliodide. The yields of the desired sulfoxonium salts by this method are usually poor except that of trimethylsulfoxonium iodide, Diarylalkyl- or triaryl-sulfoxonium ions can not be prepared by this alkylation.

The synthesis and ring opening of N‐substituted‐2‐oxo‐6‐azaspiro[2,5] octanes

AbstractN‐Substituted‐4‐piperidones have been reacted with trimethyl sulfoxonium iodide to give the title compounds. These undergo ring opening with lithium aluminum hydride‐aluminum chloride to give piperidine‐4‐methanols which were converted to the chloromethylpiperidines.

A convenient and economical preparation of l-methionine-methyl- d3

The thermal decomposition of nonadeuterio trimethylsulfoxonium iodide, prepared from the nondeuterated salt and deuterium oxide, gives a high yield of methyl- d 3 iodide. Direct alkylation of the l-homocysteine anion, generated by the sodium-liquid ammonia reduction of l-methionine by methyl- d 3iodide gives optically pure l-methionine-methyl- d 3. A procedure for the preparation of tritiated compounds is also developed.

Studies on phenoxazine related compounds. IV. Reaction of imidazo (4,5,1-kl)phenoxazine and trimethylsulfoxonium iodide

Reaction of imidazo [4, 5, 1-kl] phenoxazine (I) with trimethylsulfoxonium iodide (TMSI), prepared from DMSO with methyl iodide, in DMSO at 105° under nitrogen atmosphere gave 2-methyl-1, 2-dihydroimidazo [4, 5, 1-kl] phenoxazin-1-one (III). Similar reaction of I with TMSI in propanol or diethylene glycol afforded 1-methyl-(formyl) aminophenoxazine (V). The synthetic mechanisms of III and V were clarified.