The Metalation of Phenoxathiin

Gilman, Henry; Ess, Marian W. Van; Willis, H. B.; Stuckwisch, C. G.

doi:10.1021/ja01867a007

Cited by 23 publications

(11 citation statements)

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“…148-149°C. Gilman, Van Ess, Willis, and Stuckwisch (11) showed that phenoxathiin undergoes metalation with n-butyllithium in the 4-position by conversion of the organometallic compound so formed into 4-chlorophenoxathiin-10-dioxide according to the following scheme: One dichlorophenoxathiin has been prepared. Its 10-oxide was obtained in 25 per cent yield by treating "p-chlorophenol-o-sulfoxide" with cold concentrated sulfuric acid.…”

Section: Halogen Derivativesmentioning

confidence: 99%

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The Chemistry of Phenoxathiin and its Derivatives.

Deasy¹

1943

Chem. Rev.

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Section: Halogen Derivativesmentioning

confidence: 99%

“…Gilman, Van Ess, Willis, and Stuckwisch (11) obtained a yield of over 50 per cent of purified phenoxathiin-2-carboxylic acid (m.p. 260-265°C.)…”

Section: Hydroxy Derivativesmentioning

confidence: 99%

The Chemistry of Phenoxathiin and its Derivatives.

Deasy¹

1943

Chem. Rev.

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“…The method of preparation for phenoxathiin has been used most widely encountered is the reaction between diphenyl ether and sulfur in the presence of anhydrous aluminum chloride [2,3]. Large number has been proposed for phenoxathiin and some of its derivatives, recently addition of phenoxathiincation radical to a cyclic alkene in acetonitril (MeCN) solution occurred stereo specifically to form bis(10-phenoxathiiniumyl) alkane adducts [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Isoxazolin - Phenoxathiin Derivatives

Mohamad¹,

AL-Araji

2017

JNUS

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The aim of the present work is synthesis of new phenoxathiin derivatives. The 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) obtained from the reaction 2-acetylphenoxathiin with different aromatic aldehyde in the presence of sodium hydroxide. The reaction of 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) with hydroxylamine hydrochloride in ethanolic sodium hydroxide solution to get 2-(isoxazolin-3-yl) phenoxathiin derivatives (4a-4j) which substituted at position (5) in isoxazoline ring with different aryl groups according to aromatic aldehyde used in the preparation of (3a-3j). All the synthesized compounds were characterized by different identification techniques to confirm structure which has been obtained.

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“…Phenoxathiin is given as the preferred name by Patterson and Capell [1][2][3]. Most widely method of preparation of phenoxathiinhas been used alkyl phenoxathiinoxides by Ferrario [4][5][6][7][8][9][10]and dioxides of cycloalkylphenoxathiins and their halogen derivatives have been recommended as modifiers in plastic materials, intermediates antioxidants and as rubber and gum inhibitors [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Pyrazoline - Phenoxathiin Derivatives

AL-Araji¹,

Mohamad²

2013

Baghdad Sci.J

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Phenoxathiin was prepared by the reaction of diphenyl ether with sulfur in the presence of anhydrous aluminum chloride. This work comprised the synthesis of new phenoxathiin derivatives containing heterocyclic moieties. These heterocyclic compounds were synthesized in three groups. The first group was made up of 2-(oxoalken-1-yl) phenoxathiin derivatives (3a-3j) obtained from the reaction of 2-acetylphenoxathiin with different aromatic aldehyde in the presence of sodium hydroxide. The other two groups involved compounds produced from the reaction of (3a-3j) with hydrazine hydrate in acetic acid to get 2-(1-acetyl pyrazolin-3-yl) phenoxathiin derivatives (4a-4j), and phenyl hydrazine in the presence of piperidine to afford 2-(1-phenyl pyrazolin-3-yl) phenoxathiin derivatives (5a-5j). All these compounds of two groups above were substituted in position (5) in pyrazoline ring with different aryl groups according to aromatic aldehyde used in the preparation of the first group series compounds.

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The Metalation of Phenoxathiin

Cited by 23 publications

References 0 publications

The Chemistry of Phenoxathiin and its Derivatives.

The Chemistry of Phenoxathiin and its Derivatives.

Synthesis of New Isoxazolin - Phenoxathiin Derivatives

Synthesis of New Pyrazoline - Phenoxathiin Derivatives

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