Publication:
Electrophilic difluoro(phenylthio)methylation: Generation, stability, and reactivity of α-fluorocarbocations

Issued Date

2013-11-15

Resource Type

Article

ISSN

15237052
15237060

DOI

10.1021/ol402631t

Other identifier(s)

2-s2.0-84887968286

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Organic Letters. Vol.15, No.22 (2013), 5666-5669

Suggested Citation

Nolan M. Betterley, Panida Surawatanawong, Samran Prabpai, Palangpon Kongsaeree, Chutima Kuhakarn, Manat Pohmakotr, Vichai Reutrakul Electrophilic difluoro(phenylthio)methylation: Generation, stability, and reactivity of α-fluorocarbocations. Organic Letters. Vol.15, No.22 (2013), 5666-5669. doi:10.1021/ol402631t Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/31164

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Title

Electrophilic difluoro(phenylthio)methylation: Generation, stability, and reactivity of α-fluorocarbocations

Author(s)

Nolan M. Betterley
 Panida Surawatanawong
 Samran Prabpai
 Palangpon Kongsaeree
 Chutima Kuhakarn
 Manat Pohmakotr
 Vichai Reutrakul

Other Contributor(s)

Mahidol University

Abstract

Electrophilic difluoro(phenylthio)methylation of allylsilanes has been achieved using bromodifluoro(phenylthio)methane (PhSCF2Br) and silver hexafluoroantimonate (AgSbF6). The structural assignment and observation of α-fluorocarbocation were substantiated by NMR and theoretical calculations. Detailed mechanistic and electronic studies have provided a fundamental understanding of the reactivity and stability of the difluoro(phenylthio)methylium cation (PhSCF2+). © 2013 American Chemical Society.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/31164

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