Publication:
α,α-Difluoro-α-phenylsulfanylmethyl carbanion equivalent: a novel gem-difluoromethylenation of carbonyl compounds

Issued Date

2006-06-19

Resource Type

Article

ISSN

00404020

DOI

10.1016/j.tet.2006.04.015

Other identifier(s)

2-s2.0-33646549878

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron. Vol.62, No.25 (2006), 5973-5985

Suggested Citation

Manat Pohmakotr, Kanhokthron Boonkitpattarakul, Winai Ieawsuwan, Suwatchai Jarussophon, Nongnaphat Duangdee, Patoomratana Tuchinda, Vichai Reutrakul α,α-Difluoro-α-phenylsulfanylmethyl carbanion equivalent: a novel gem-difluoromethylenation of carbonyl compounds. Tetrahedron. Vol.62, No.25 (2006), 5973-5985. doi:10.1016/j.tet.2006.04.015 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/23022

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Title

α,α-Difluoro-α-phenylsulfanylmethyl carbanion equivalent: a novel gem-difluoromethylenation of carbonyl compounds

Author(s)

Manat Pohmakotr
 Kanhokthron Boonkitpattarakul
 Winai Ieawsuwan
 Suwatchai Jarussophon
 Nongnaphat Duangdee
 Patoomratana Tuchinda
 Vichai Reutrakul

Other Contributor(s)

Mahidol University
 Thailand Ministry of Science and Technology

Abstract

α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3) has been demonstrated as an α,α-difluoro-α-phenylsulfanylmethyl carbanion equivalent. gem-Difluorophenylsulfanylmethylation of carbonyl compounds has been successfully achieved by using PhSCF2SiMe3in the presence of TBAF in THF. The adducts have been converted to the corresponding gem-difluoroalkenes by a novel pyrolytic and/or FVP elimination of the β-hydroxy-α-phenylsufinyl derivatives under reduced pressure. © 2006 Elsevier Ltd. All rights reserved.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/23022

Collections

Scopus 2006-2010