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 | |
| Publication status | Published - 2003 Sep 1 |
Keywords
- Carbocyclization
- Difluoroolefin
- Fluorocyclopentane
- Fluorocyclopentene
- SnCl
ASJC Scopus subject areas
- Biochemistry
- Environmental Chemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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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