Thioiminium and thiaphospholanium derived from acetonitrile via nickel(II)-(2-mercaptophenyl)phosphine complexation

Hao Ching Chang; Yu Chen Hsu; Chia Hui Chen; Ting Shen Kuo; Way Zen Lee

doi:10.1039/c5dt03316k

Thioiminium and thiaphospholanium derived from acetonitrile via nickel(II)-(2-mercaptophenyl)phosphine complexation

Hao Ching Chang, Yu Chen Hsu, Chia Hui Chen, Ting Shen Kuo, Way Zen Lee^*

^*Corresponding author for this work

Department of Chemistry

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

5 Citations (Scopus)

Abstract

[Ni(P(o-C₆H₄S)(o-C₆H₄SC(CH₃)NH₂)(C₆H₅))₂](ClO₄)₂ (2) with two thioiminium functionalities is derived from CH₃CN solvent under anhydrous conditions. Moreover, thiaphospholanium salts, [(C₆H₅)P(C₆H₄SC(CH₃)(NHCOCH₃))(o-C₆H₄SH)](ClO₄) (3) and [(C₆H₅)₂-P(C₆H₄SC(CH₃)(NH₃))](ClO₄)₂ (5), can be obtained through a similar Pinner-type nitrile activation. These results demonstrate the possible intermediate of enzymatic nitrile transformation and also provide an approach to the preparation of 2-amino-1,3-benzothiaphospholanium derivatives.

Original language	English
Pages (from-to)	20808-20811
Number of pages	4
Journal	Dalton Transactions
Volume	44
Issue number	48
DOIs	https://doi.org/10.1039/c5dt03316k
Publication status	Published - 2015

ASJC Scopus subject areas

Inorganic Chemistry

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10.1039/c5dt03316k

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@article{09fe99acf4944cc681f28f4544412cb4,

title = "Thioiminium and thiaphospholanium derived from acetonitrile via nickel(II)-(2-mercaptophenyl)phosphine complexation",

abstract = "[Ni(P(o-C6H4S)(o-C6H4SC(CH3)NH2)(C6H5))2](ClO4)2 (2) with two thioiminium functionalities is derived from CH3CN solvent under anhydrous conditions. Moreover, thiaphospholanium salts, [(C6H5)P(C6H4SC(CH3)(NHCOCH3))(o-C6H4SH)](ClO4) (3) and [(C6H5)2-P(C6H4SC(CH3)(NH3))](ClO4)2 (5), can be obtained through a similar Pinner-type nitrile activation. These results demonstrate the possible intermediate of enzymatic nitrile transformation and also provide an approach to the preparation of 2-amino-1,3-benzothiaphospholanium derivatives.",

author = "Chang, {Hao Ching} and Hsu, {Yu Chen} and Chen, {Chia Hui} and Kuo, {Ting Shen} and Lee, {Way Zen}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2015.",

year = "2015",

doi = "10.1039/c5dt03316k",

language = "English",

volume = "44",

pages = "20808--20811",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "48",

}

TY - JOUR

T1 - Thioiminium and thiaphospholanium derived from acetonitrile via nickel(II)-(2-mercaptophenyl)phosphine complexation

AU - Chang, Hao Ching

AU - Hsu, Yu Chen

AU - Chen, Chia Hui

AU - Kuo, Ting Shen

AU - Lee, Way Zen

N1 - Publisher Copyright: © The Royal Society of Chemistry 2015.

PY - 2015

Y1 - 2015

N2 - [Ni(P(o-C6H4S)(o-C6H4SC(CH3)NH2)(C6H5))2](ClO4)2 (2) with two thioiminium functionalities is derived from CH3CN solvent under anhydrous conditions. Moreover, thiaphospholanium salts, [(C6H5)P(C6H4SC(CH3)(NHCOCH3))(o-C6H4SH)](ClO4) (3) and [(C6H5)2-P(C6H4SC(CH3)(NH3))](ClO4)2 (5), can be obtained through a similar Pinner-type nitrile activation. These results demonstrate the possible intermediate of enzymatic nitrile transformation and also provide an approach to the preparation of 2-amino-1,3-benzothiaphospholanium derivatives.

AB - [Ni(P(o-C6H4S)(o-C6H4SC(CH3)NH2)(C6H5))2](ClO4)2 (2) with two thioiminium functionalities is derived from CH3CN solvent under anhydrous conditions. Moreover, thiaphospholanium salts, [(C6H5)P(C6H4SC(CH3)(NHCOCH3))(o-C6H4SH)](ClO4) (3) and [(C6H5)2-P(C6H4SC(CH3)(NH3))](ClO4)2 (5), can be obtained through a similar Pinner-type nitrile activation. These results demonstrate the possible intermediate of enzymatic nitrile transformation and also provide an approach to the preparation of 2-amino-1,3-benzothiaphospholanium derivatives.

UR - http://www.scopus.com/inward/record.url?scp=84948845786&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84948845786&partnerID=8YFLogxK

U2 - 10.1039/c5dt03316k

DO - 10.1039/c5dt03316k

M3 - Article

AN - SCOPUS:84948845786

SN - 1477-9226

VL - 44

SP - 20808

EP - 20811

JO - Dalton Transactions

JF - Dalton Transactions

IS - 48

ER -

Thioiminium and thiaphospholanium derived from acetonitrile via nickel(II)-(2-mercaptophenyl)phosphine complexation

Abstract

ASJC Scopus subject areas

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CCDC 1420690: Experimental Crystal Structure Determination

CCDC 1420692: Experimental Crystal Structure Determination

CCDC 1420691: Experimental Crystal Structure Determination

Cite this

Thioiminium and thiaphospholanium derived from acetonitrile via nickel(II)-(2-mercaptophenyl)phosphine complexation

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1420690: Experimental Crystal Structure Determination

CCDC 1420692: Experimental Crystal Structure Determination

CCDC 1420691: Experimental Crystal Structure Determination

Cite this