Synthesis of dihydrothiophene, thiophene, and their selenium analogues carrying four phosphoryl groups

Shigeru Sasaki; Kazutaka Adachi; Masaaki Yoshifuji

doi:10.1021/ol070414y

Synthesis of dihydrothiophene, thiophene, and their selenium analogues carrying four phosphoryl groups

Shigeru Sasaki, Kazutaka Adachi, Masaaki Yoshifuji

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

Abstract

Sodium hydrosulfide undergoes addition to two molecules of bis(diethoxyphosphoryl)acetylene followed by cyclization to give a 2,3-dihydrothiophene carrying four phosphoryl groups. Oxidation of the 2,3-dihydrothiophene with mCPBA gives the corresponding sulfoxide or sulfone depending on the ratio of the reagents, and the sulfoxide is dehydrated to afford a tetraphosphorylthiophene. The corresponding dihydroselenophene and selenophene are also synthesized in a similar manner.

Original language	English
Pages (from-to)	1729-1732
Number of pages	4
Journal	Organic letters
Volume	9
Issue number	9
DOIs	https://doi.org/10.1021/ol070414y
Publication status	Published - 2007 Apr 26

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of dihydrothiophene, thiophene, and their selenium analogues carrying four phosphoryl groups",

abstract = "Sodium hydrosulfide undergoes addition to two molecules of bis(diethoxyphosphoryl)acetylene followed by cyclization to give a 2,3-dihydrothiophene carrying four phosphoryl groups. Oxidation of the 2,3-dihydrothiophene with mCPBA gives the corresponding sulfoxide or sulfone depending on the ratio of the reagents, and the sulfoxide is dehydrated to afford a tetraphosphorylthiophene. The corresponding dihydroselenophene and selenophene are also synthesized in a similar manner.",

author = "Shigeru Sasaki and Kazutaka Adachi and Masaaki Yoshifuji",

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doi = "10.1021/ol070414y",

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T1 - Synthesis of dihydrothiophene, thiophene, and their selenium analogues carrying four phosphoryl groups

AU - Sasaki, Shigeru

AU - Adachi, Kazutaka

AU - Yoshifuji, Masaaki

PY - 2007/4/26

Y1 - 2007/4/26

N2 - Sodium hydrosulfide undergoes addition to two molecules of bis(diethoxyphosphoryl)acetylene followed by cyclization to give a 2,3-dihydrothiophene carrying four phosphoryl groups. Oxidation of the 2,3-dihydrothiophene with mCPBA gives the corresponding sulfoxide or sulfone depending on the ratio of the reagents, and the sulfoxide is dehydrated to afford a tetraphosphorylthiophene. The corresponding dihydroselenophene and selenophene are also synthesized in a similar manner.

AB - Sodium hydrosulfide undergoes addition to two molecules of bis(diethoxyphosphoryl)acetylene followed by cyclization to give a 2,3-dihydrothiophene carrying four phosphoryl groups. Oxidation of the 2,3-dihydrothiophene with mCPBA gives the corresponding sulfoxide or sulfone depending on the ratio of the reagents, and the sulfoxide is dehydrated to afford a tetraphosphorylthiophene. The corresponding dihydroselenophene and selenophene are also synthesized in a similar manner.

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Synthesis of dihydrothiophene, thiophene, and their selenium analogues carrying four phosphoryl groups

Abstract

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