Archives of Pharmacal Research
- Volume 10 Issue 4
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- Pages.239-244
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- 1987
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- 0253-6269(pISSN)
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- 1976-3786(eISSN)
Allylic fluorination
- Park, Oee-Sook (College of Natural Sciences, Chungbuk National University) ;
- Son, Hoe-Joo (College of Natural Sciences, Chungbuk National University) ;
- Lee, Woo-Young (Department of Chemistry, Seoul National University)
- Published : 1987.12.01
Abstract
An efficient and inexpensive method for the substitution of allylic hydroxyl group with fluoride, without allylic rearrangement, and elimination was developed. This method consists of treating an allylic alcohol with methylithium, followed by p-toluene sulfonyl fluoride, lithium fluoride and 12-Crown-4. This methodology was proved to be efficient by preparting geranyl fluoride, neryl fluoride, cinnamyl fluoride, E, E-farnesyl fluoride, retinyl fluoride and 4-fluoro-2-methyl-6-(ptolyl)-2-heptene.
Keywords
- Crown ether;
- Regio and stereochemical problem;
- Geranyl fluoride;
- Neryl fluoride;
- Cinnamyl fluoride;
- E,E-farnesyl fluoride;
- Retinyl fluoride;
- 4-Fluoro-2-methyl-6-(p-tolyl)-2-heptene