5684-29-7

Upstream product

• 79958-79-5 N-(3-hydroxypropylthio)phthalimide 

Downstream Products

• 1120-71-4 1,3-propanesultone 
• 24308-28-9 1,3-propanesultine 
• 30453-21-5 3-[(3-hydroxypropyl)disulfanyl]-1-propanol 
• 20291-59-2 3-mercaptopropanal 
• 107-18-6 allyl alcohol 
• 107-02-8 acrolein 

Relevant academic research and scientific papers

Fungicidal oxathiin azoles

This invention relates to a novel class of azoles of 5,6-dihydro-1,4-oxathins having fungicidal activity. The class of compounds is represented by formula (I) STR1 wherein R is each independently halogen; trifluoromethyl; C1 -C8 alkyl; C3 -C6 cycloalkyl; C1 -C8 alkoxy; C1 -C8 alkoxycarbonyl; amino; substituted amino; aminocarbonyl; aminosulfonyl; C1 -C8 alkoxy sulfonyl; phenyl; phenoxy; phenyl or phenoxy mono-, di- or tri-substituted independently with halogen, trifluoromethyl, C1 -C8 alkyl or C1 -C8 alkoxy; or benzyl; G is CH or N; m is 0 1 or 2; and n is 0, 1 or 2. Fungicidal compositions, methods of controlling fungi and methods for preparing the compounds are within the scope of the invention.

Thermal Decomposition of 1,2-Oxathiolane in the Gas Phase

The cyclic sulfenic ester 1,2-oxathiolane (1) decomposes thermally (400 - 450 K) exclusively to give acrolein (3) via 3-mercaptopropanal (2) by loss of hydrogen sulfide.Isotopic labelling experiments reveal the presence of a 1,2-oxathiolane-thietane 1-oxide equilibrium (1 4).

Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

This method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide is based on the use of an oxathiolane, namely, 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide, which may be formed by condensing 2-mercaptoethanol with acetoacetanilide under acidic conditions in a solvent medium (aromatic hydrocarbon, chlorinated hydrocarbon or alkyl ester of an aliphatic acid). The said oxathiolane, with or without purification, is reacted with hydrogen peroxide in water or in a water-organic solvent mixture under basic conditions in the presence of a catalytic amount of a metal compound such as sodium tungstate to form 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide. The said oxathiolane oxide, while dissolved in a chlorinated hydrocarbon or an alkyl ester of an aliphatic carboxylic acid, or while suspended in an aromatic hydrocarbon, is subjected to a ring expansion reaction by heating under acidic conditions in the presence of a catalytic quantity of a sulfonium, sulfoxonium or phosphonium compound, to form 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide with evolution of water. The product is a known bactericide and fungicide.

1,2-Oxathiolan, a Simple Sultene

Evidence is presented which indicates that pyrolysis of N-(3-hydroxypropylthio)phthalimide gives 1,2-oxathiolan as a volatile product via an intermediate tentatively identified as a cyclic oligomer.

Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

This method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide is based on the use of an oxathiolane, namely, 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide, which may be formed by condensing 2-mercaptoethanol with acetoacetanilide under acidic conditions in a solvent medium (aromatic hydrocarbon, chlorinated hydrocarbon or alkyl ester of an aliphatic acid). The said oxathiolane, with or without purification, is reacted with hydrogen peroxide in water or in a water-organic solvent mixture under basic conditions in the presence of a catalytic amount of a metal compound such as sodium tungstate to form 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide. The said oxathiolane oxide, while dissolved in a chlorinated hydrocarbon or an alkyl ester of an aliphatic carboxylic acid, or while suspended in an aromatic hydrocarbon, is subjected to a ring expansion reaction by heating under acidic conditions in the presence of a catalytic quantity of a quaternary ammonium salt to form 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide with evolution of water. The product is a known bactericide and fungicide.