Journal of Fluorine Chemistry p. 117 - 127 (1999)
Update date:2022-08-03
Topics:
Ameduri
Boutevin
Kostov
Petrova
The synthesis of the new halogenated alcohol BrCF2CFClCH2CHICH2OH as a precursor of 4,5,5 trifluoro-4-ene pentanol F2C=CFC3H6OH is based on a two-step process. First, the radical addition of iodine monobromide to chlorotrifluoroethylene (CTFE) led to the expected BrCF2CFClI (I) and ICF2CFClBr (II), but also to BrCF2CFClBr (III) and ICF2CFClI (IV), the amount of which determined by 19F NMR depended on the reaction conditions: by feeding CTFE into IBr continuously or in batches; photochemical or thermal initiations, and with various initial [IBr]0/[CTFE]0 molar ratios. In most cases, isomer (I) was mainly produced. The second step concerned the addition of such a mixture to allyl alcohol yielding the polyhalogenoalcohol with a quantitative conversion of (I). The reactivity of different halogeno end-groups of these isomers toward the allyl alcohol was discussed. Reduction of the iodine atom into hydrogen and the halogenated alcohol was accompanied by that of the bromine atom leading to BrCF2CFClC3H6OH and HCF2CFClC3H6OH (V). Dehalogenation of the former alcohol in the presence of zinc led to F2C=CFC3H6OH while dehydrochlorination of (V) into trifluorovinyl hydroxy monomers was achieved in the presence of potassium hydroxide but in poor yields. Strategies starting from the radical additions of iodine monochloride and of iodine monobromide were compared showing that the former led to better overall yields of trifluorovinyl alcohol than the latter.
View MoreShaanxi HuaTai Bio-fine chemical company Ltd
Contact:86-029-87862197
Address:No. 5, 3rd Floor, 29 Yanta North Road, Beilin Dist.
Contact:27-792-602929
Address:SIDNEY MUFAMADI STREET 009949 X44 0700 POLOKWANE,LIMPOPO
Shanghai Sunwise Chemical Co., Ltd
website:http://www.sunwisechem.com
Contact:86-021-33883180
Address:Room 10E, Building G, Westlink Center, No. 2337 Gudai Road, Minhang District, Shanghai, China PC: 201100
PharmaResources(Kaiyuan)CO,.Ltd
Contact:+86-21-50720028
Address:No.3, Beihuan Road, Economic Development District, Kaiyuan City, Tieling City, Liaoning Province, China 112300
Penglai Qianwei Chemical Co., Ltd.
Contact:86-535-3357802
Address:Shahelu (north), Penglai, Shandong, China
Doi:10.1021/ja00375a011
(1982)Doi:10.1016/0040-4039(92)88109-I
(1992)Doi:10.1016/S0008-6215(00)81038-1
(1982)Doi:10.1021/jo01095a023
(1958)Doi:10.1021/acs.orglett.9b03001
(2019)Doi:10.1021/ja00378a023
(1982)