Novel reaction of acetylsulfenyl chloride with activated aromatic compounds

Fujisawa, Tamotsu; Kobayashi, Norio

doi:10.1021/jo00822a017

Cited by 8 publications

(1 citation statement)

References 6 publications

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“…Methods for the synthesis of compound 1 had been reported [16,17]. However, the method used in the present work had the advantage over these reported methods in that reactions are carried out under mild conditions and the reaction products are easily isolated and purification by recrystallisation from petroleum is less cumbersome.…”

Section: Introductionmentioning

confidence: 97%

<b>Synthesis and fungicidal activity of acetyl substituted benzyl disulfides</b>

Ayodele

Olajire

Amuda

et al. 2003

Bull. Chem. Soc. Eth.

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Section: Introductionmentioning

confidence: 97%

<b>Synthesis and fungicidal activity of acetyl substituted benzyl disulfides</b>

Ayodele

Olajire

Amuda

et al. 2003

Bull. Chem. Soc. Eth.

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ChemInform Abstract: EINE NEUE RK. VON ACETYLSULFENYLCHLORID MIT AKTIVIERTEN AROMATEN

Fujisawa¹,

Kobayashi²

1972

Chemischer Informationsdienst

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Sulfur‐containing polymers. VI. Preparation of poly[alkylene bis(oxycarbonyl) disulfides] and related polymers

Kobayashi

Fujisawa

1972

J. Polym. Sci. A‐1 Polym. Chem.

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synopsisPoly[alkylene bis(oxyc!arbonyl) disulfides] have been prepared for the first time by the reductive Goupling of alkylene bis(oxycarbonylsulfeny1 chlorides). Potassium iodide and a variety of transition metals or their salts were employed as reducing agents. Of these potassium iodide and cuprous chloride gave the best results. Pyrolysis, desulfurization, and thiol-indud fragmentation of the polymers have been studied. Homologous polymers, i.e., monosulfide polymer, trisulfide polymer, and tetrasulfide polymer, have been also synthesized. Monosulfide and disulfide polymers were highly crystalline solids. Trisuliide polymer was a white solid with a low degree of crystallinity. These polymers were soluble in chloroform and dichloromethane. Tetrasulfide polymer was a crystalline yellow solid and was soluble only in HMPA. RESULTS AND DISCUSSION Reductive Coupling of Alkylene Bis(oxycarbonylsdfeny1 Chlorides)Alkylene bis(oxycarbonylsulfeny1 chlorides) (I) were prepared by the reaction of chlorocarbonylsulfenyl chloride with diols as previously described [eq. (l)]." 3317 0 1972 by John Wiley & Sons, Inc. 3318 KOBAYASHI AND FUJISAWA ClCSCl + HO(CH2),0H -C1SCO(CH2),0CSC1 (1) II 0 11 0 I1 0 I a , m = 4 b , m = 6Compounds Ia and Ib are relatively stable at room temperature and therefore might be handled more easily than alkylene bis(sulfeny1 chlorides) .' en Reductive coupling of I proceeds according to eq. (2). IIa, m = 4 b , m = 6Polymer formation was performed by stirring a mixture of I and an excess of reducing agent at room temperature. As reducing agents, potassium iodide and a variety of transition metals or their salts were employed.

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Novel reaction of acetylsulfenyl chloride with activated aromatic compounds

Cited by 8 publications

References 6 publications

<b>Synthesis and fungicidal activity of acetyl substituted benzyl disulfides</b>

<b>Synthesis and fungicidal activity of acetyl substituted benzyl disulfides</b>

ChemInform Abstract: EINE NEUE RK. VON ACETYLSULFENYLCHLORID MIT AKTIVIERTEN AROMATEN

Sulfur‐containing polymers. VI. Preparation of poly[alkylene bis(oxycarbonyl) disulfides] and related polymers

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