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

doi:10.1016/S0022-1139(03)00138-6

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 language	English
Pages (from-to)	75-80
Number of pages	6
Journal	Journal of Fluorine Chemistry
Volume	123
Issue number	1
DOIs	https://doi.org/10.1016/S0022-1139(03)00138-6
Publication status	Published - 2003 Sep 1
Externally published	Yes

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Keywords

Carbocyclization
Difluoroolefin
Fluorocyclopentane
Fluorocyclopentene
SnCl

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry
Materials Chemistry
Polymers and Plastics

Cite this

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, 123(1), 75-80. https://doi.org/10.1016/S0022-1139(03)00138-6

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title = "Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amine",

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.",

keywords = "Carbocyclization, Difluoroolefin, Fluorocyclopentane, Fluorocyclopentene, SnCl",

author = "Akio Saito and Midori Okada and Yuko Nakamura and Osamu Kitagawa and Hiroaki Horikawa and Takeo Taguchi",

year = "2003",

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doi = "10.1016/S0022-1139(03)00138-6",

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T1 - Carbocyclization reactions of terminally difluorinated alkenyl active methine compounds mediated by SnCl4 and amine

AU - Saito, Akio

AU - Okada, Midori

AU - Nakamura, Yuko

AU - Kitagawa, Osamu

AU - Horikawa, Hiroaki

AU - Taguchi, Takeo

PY - 2003/9/1

Y1 - 2003/9/1

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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U2 - 10.1016/S0022-1139(03)00138-6

DO - 10.1016/S0022-1139(03)00138-6

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VL - 123

SP - 75

EP - 80

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

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10.1016/S0022-1139(03)00138-6