Methylthiomethyl P-tolyl Sulfone Research Articles

Novel Synthesis of α‐Amino Carboxamides and Their Related Compounds via α‐Oxo Sulfones Starting from 2,2‐Disulfonyloxiranes.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Novel Synthesis of α-Amino Carboxamides and Their Related Compounds via α-Oxo Sulfones Starting from 2,2-Disulfonyloxiranes

Abstract 2-(Methylsulfonyl)-2-(p-tolylsulfonyl)oxiranes 1 are easily prepared by the condensation of methylthiomethyl p-tolyl sulfone (MT-sulfone) with aldehydes and the subsequent oxidation with MCPBA. They smoothly reacted with 2 molar amounts of primary or secondary amines to give α-amino carboxamides in high yield. This reaction can be suitably extended to the reaction with one molar amount of 1,n-diaminoalkanes (n = 2, 3, or 4) to form the corresponding 2,5-diazacyclohexanone, 2,6-diazacycloheptanone, or 2,7-diazacyclooctanone, respectively. The reaction of 1 with some related compounds having two nucleophilic sites are also described.

Nickel- or Iron-Catalyzed Coupling of Lithiated Methylthiomethylp-Tolyl Sulfone with Lithiated Alkyl Sulfones to Give Methylthioalkenes

The reaction of methylthiomethyl p-tolyl sulfone with alkyl sulfones when lithiated gives regioselectively vinyl sulfides in high yields in the presence of Ni(acac)2 or Fe(acac)3.

ChemInform Abstract: Development of Sulfur Compounds as Synthetic Reagents

Combinations of a thio group and a sulfonyl group have proven to be useful for development of synthetic reagents. Now, I describe organic syntheses using methylthiomethyl p-tolyl sulfone (MT-sulfone) and 3-(methylthio)-2-propenyl p-tolyl sulfone which are prepared from easily obtainable DMSO and 1,3-dichloropropene, respectively.

ChemInform Abstract: Reactions of Quinoline and 4‐Chloroquinoline 1‐Oxides with Phenoxyacetonitrile, Chloromethyl Phenyl Sulfone, and Methylthiomethyl p‐Tolyl Sulfone.

ChemInformVolume 18, Issue 26 Heterocyclic Compounds ChemInform Abstract: Reactions of Quinoline and 4-Chloroquinoline 1-Oxides with Phenoxyacetonitrile, Chloromethyl Phenyl Sulfone, and Methylthiomethyl p-Tolyl Sulfone. M. HAMANA, M. HAMANA Central Res. Lab., Chugai Pharm. Co., Ltd., Tokyo 171, JapanSearch for more papers by this authorY. FUJIMURA, Y. FUJIMURA Central Res. Lab., Chugai Pharm. Co., Ltd., Tokyo 171, JapanSearch for more papers by this authorT. HARADAHIRA, T. HARADAHIRA Central Res. Lab., Chugai Pharm. Co., Ltd., Tokyo 171, JapanSearch for more papers by this author M. HAMANA, M. HAMANA Central Res. Lab., Chugai Pharm. Co., Ltd., Tokyo 171, JapanSearch for more papers by this authorY. FUJIMURA, Y. FUJIMURA Central Res. Lab., Chugai Pharm. Co., Ltd., Tokyo 171, JapanSearch for more papers by this authorT. HARADAHIRA, T. HARADAHIRA Central Res. Lab., Chugai Pharm. Co., Ltd., Tokyo 171, JapanSearch for more papers by this author First published: June 30, 1987 https://doi.org/10.1002/chin.198726184Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume18, Issue26June 30, 1987 RelatedInformation

Development of sulfur compounds as synthetic reagents

Abstract

A novel preparation of 3-methylthio-2-oxopropanal acetals using methylthiomethyl p-tolyl sulfone

Treatment of an alkoxyacetyl derivative ( 3) of methylthiomethyl p-tolyl sulfone ( 1), easily obtainable from an alkoxyacetic ester and 1, with such a base as triethylamine or DABCO affords 3-methylthio-2-oxopropanal acetal (4).

Reduction of Ketene Dithioacetal S,S-Dioxides with Sodium Borohydride and Its Application to a Convenient Synthesis of Alkyl Arylmethyl Ketones

Abstract The C–C double bond of a ketene dithioacetal S,S-dioxide was found to undergo reduction with sodium borohydride. This fact provides an efficient synthetic route from an aromatic aldehyde to an alkyl arylmethyl ketone using methylthiomethyl p-tolyl sulfone.

A versatile reagent for synthesis of α-hydroxy aldehydes and ketones —methylthiomethyl p-tolyl sulfone

Methylthiomethyl p-tolyl sulfone ( 1) can be utilised for synthesizing α-hydroxy ketones as well as α-hydroxy aldehydes, the hydroxyl group of which is protected with acetyl, tetrahydropyranyl, or methoxymethyl group.

Aldehyde and ketone syntheses using methylthiomethyl p-tolyl sulfone

Methylthiomethyl p-tolyl sulfone (1) was conveniently alkylated to give mono- and dialkylated products (2 and 4). Reaction conditions for the trasformation of 2 and 4 into aldehydes (3) and ketones (5), respectively, were exploited.

ChemInform Abstract: CONVENIENT PREPARATION OF METHYLTHIOMETHYL P‐TOLYL SULFONE STARTING FROM DIMETHYL SULFOXIDE

An efficient method for preparing methylthiomethyl p-tolyl sulfone was accomplished by the Pummerer reaction of dimethyl sulfoxide with acetic anhydride followed by treatment of the resulting acetoxymethyl methyl sulfide with sodium p-toluenesulfinate in the presence of sodium acetate in acetic acid.

ＭＴ‐スルホン 期待される有機硫黄合成試剤

MT-sulfone is the abbreviation for methylthiomethyl p-tolyl sulfone (1), which is easily obtainable from DMSO in one-pot manner : treatment of DMSO with acetic anhydride followed by the reaction of the resulting acetoxymethyl methyl sulfide with sodium p-toluenesulfinate in acetic acid. This reagent is thermally stable and less hygroscopic, and a carbanion can be generated on the central carbon of 1 with an easily handled base such as sodium hydride or sodium hydroxide-TOMAC (a phase transfer catalyst). Hence MT-sulfone (1) has been revealed to be an efficient reagent for preparing many kinds of organic compounds such as carboxylic esters, S-methyl carbothioate, aldehydes, acyclic and cyclic ketones, α-alkoxy-α-arylacetic esters, S-methyl α-ketocarbothioate, and various derivatives of 2-methoxycarbonyl-1, 4-cyclohexanedione.

Convenient Preparation of Methylthiomethyl p-Tolyl Sulfone Starting from Dimethyl Sulfoxide

Abstract An efficient method for preparing methylthiomethyl p-tolyl sulfone was accomplished by the Pummerer reaction of dimethyl sulfoxide with acetic anhydride followed by treatment of the resulting acetoxymethyl methyl sulfide with sodium p-toluenesulfinate in the presence of sodium acetate in acetic acid.

ChemInform Abstract: UTILIZATION OF METHYLTHIOMETHYL P‐TOLYL SULFONE IN ORGANIC SYNTHESIS

Chemischer InformationsdienstVolume 14, Issue 43 Isocyclic Compounds ChemInform Abstract: UTILIZATION OF METHYLTHIOMETHYL P-TOLYL SULFONE IN ORGANIC SYNTHESIS K. OGURA, K. OGURASearch for more papers by this authorN. YAHATA, N. YAHATASearch for more papers by this authorK. HASHIZUME, K. HASHIZUMESearch for more papers by this authorK. TSUYAMA, K. TSUYAMASearch for more papers by this authorK. TAKAHASHI, K. TAKAHASHISearch for more papers by this authorH. IIDA, H. IIDASearch for more papers by this author K. OGURA, K. OGURASearch for more papers by this authorN. YAHATA, N. YAHATASearch for more papers by this authorK. HASHIZUME, K. HASHIZUMESearch for more papers by this authorK. TSUYAMA, K. TSUYAMASearch for more papers by this authorK. TAKAHASHI, K. TAKAHASHISearch for more papers by this authorH. IIDA, H. IIDASearch for more papers by this author First published: October 25, 1983 https://doi.org/10.1002/chin.198343196Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume14, Issue43October 25, 1983 RelatedInformation

A novel route from a carboxylic acid to a carbaldehyde using methylthiomethyl p-tolyl sulfone

A new conversion of a carboxylic ester to a carbaldehyde involving formation and dissociation of a CC bond at the acyl carbon was accomplished by the use of methylthiomethyl p-tolyl sulfone ( 1 ).