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 journal › Article

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 journal › Article

Saito, A, Okada, M, Nakamura, Y, Kitagawa, O, Horikawa, H & Taguchi, T 2003, 'Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amine', Journal of Fluorine Chemistry, vol. 123, no. 1, pp. 75-80. https://doi.org/10.1016/S0022-1139(03)00138-6
Saito A, Okada M, Nakamura Y, Kitagawa O, Horikawa H, Taguchi T. Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amine. Journal of Fluorine Chemistry. 2003 Sep 1;123(1):75-80. https://doi.org/10.1016/S0022-1139(03)00138-6
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 - Saito, Akio

AU - Okada, Midori

AU - Nakamura, Yuko

AU - Kitagawa, Osamu

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.

KW - Carbocyclization

KW - Difluoroolefin

KW - Fluorocyclopentane

KW - Fluorocyclopentene

KW - SnCl

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