Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amine

Akio Saito, Midori Okada, Yuko Nakamura, Osamu Kitagawa, Hiroaki Horikawa, Takeo Taguchi

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Carbocyclization of terminally difluorinated 3-butenyl active methine compounds 1a-1e proceeded through the 5- endo mode, upon treating with SnCl4 and triethylamine to give fluorocyclopentene derivatives 3a-3e. Iodocarbocyclization of dimethyl 2-(4,4-difluorobut-3-enyl)malonate (1a) mediated by I2, SnCl4 and amine provided 2,2-difluoro-3-iodocyclopentane-1, 1-dicarboxylate 4a through the 5-endo mode, while in the case of 2-(5,5-difluoropent-4-enyl)malonate (1f) 5-exo mode cyclization reaction took place to give difluoroiodomethylcyclopentane derivative 5f.

Original languageEnglish
Pages (from-to)75-80
Number of pages6
JournalJournal of Fluorine Chemistry
Volume123
Issue number1
DOIs
Publication statusPublished - 2003 Sep 1
Externally publishedYes

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Amines
amines
Derivatives
Cyclization
stannic chloride
malonic acid
amine
triethylamine

Keywords

  • Carbocyclization
  • Difluoroolefin
  • Fluorocyclopentane
  • Fluorocyclopentene
  • SnCl

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics

Cite this

Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amine. / Saito, Akio; Okada, Midori; Nakamura, Yuko; Kitagawa, Osamu; Horikawa, Hiroaki; Taguchi, Takeo.

In: Journal of Fluorine Chemistry, Vol. 123, No. 1, 01.09.2003, p. 75-80.

Research output: Contribution to journalArticle

Saito, Akio ; Okada, Midori ; Nakamura, Yuko ; Kitagawa, Osamu ; Horikawa, Hiroaki ; Taguchi, Takeo. / Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amine. In: Journal of Fluorine Chemistry. 2003 ; Vol. 123, No. 1. pp. 75-80.
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AU - Nakamura, Yuko

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AU - Horikawa, Hiroaki

AU - Taguchi, Takeo

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N2 - Carbocyclization of terminally difluorinated 3-butenyl active methine compounds 1a-1e proceeded through the 5- endo mode, upon treating with SnCl4 and triethylamine to give fluorocyclopentene derivatives 3a-3e. Iodocarbocyclization of dimethyl 2-(4,4-difluorobut-3-enyl)malonate (1a) mediated by I2, SnCl4 and amine provided 2,2-difluoro-3-iodocyclopentane-1, 1-dicarboxylate 4a through the 5-endo mode, while in the case of 2-(5,5-difluoropent-4-enyl)malonate (1f) 5-exo mode cyclization reaction took place to give difluoroiodomethylcyclopentane derivative 5f.

AB - Carbocyclization of terminally difluorinated 3-butenyl active methine compounds 1a-1e proceeded through the 5- endo mode, upon treating with SnCl4 and triethylamine to give fluorocyclopentene derivatives 3a-3e. Iodocarbocyclization of dimethyl 2-(4,4-difluorobut-3-enyl)malonate (1a) mediated by I2, SnCl4 and amine provided 2,2-difluoro-3-iodocyclopentane-1, 1-dicarboxylate 4a through the 5-endo mode, while in the case of 2-(5,5-difluoropent-4-enyl)malonate (1f) 5-exo mode cyclization reaction took place to give difluoroiodomethylcyclopentane derivative 5f.

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