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 › peer-review

29 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

Keywords

Carbocyclization
Difluoroolefin
Fluorocyclopentane
Fluorocyclopentene
SnCl

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/S0022-1139(03)00138-6

Cite this

@article{3d81314ba6544dadb662d8f54b12ae6b,

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",

month = sep,

day = "1",

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

language = "English",

volume = "123",

pages = "75--80",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier BV",

number = "1",

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TY - JOUR

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

IS - 1

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