80363-03-7Relevant academic research and scientific papers
Investigation of the factors controlling the regioselectivity of the hydroboration of fluoroolefins
Ramachandran, P. Veeraraghavan,Jennings, Michael P.
, p. 386 - 387 (2002)
Either Markovnikov or anti-Markovnikov regioselectivity can be achieved at will during the hydroboration-oxidation of perfluoroalkyl(aryl)ethylenes by varying the hydroborating agent.
SOME APPROACHES TO THE SYNTHESIS OF FLUORINATED ALCOHOLS AND ESTERS. II. USE OF F-ALKYL IODIDES FOR THE SYNTHESIS OF F-ALKYL ALKANOLS
Brace, Neal O.
, p. 313 - 328 (2007/10/02)
Free radical addition of an F-alkyl iodide (RFI) to an alkenol or ester, followed by appropriate reduction is an efficient method for preparating the corresponding F-alkyl-alkanols of the homologous series, RF(CH2)nOH.When n=2, 4 or higher, the two steps take place smoothly.The 1,2,3-substituted systems RFCH2CHYCH2Z, however, are susceptible to surprising difficulties.Reduction of RFCH2CHICH2OH to RF(CH2)3OH by hydrogen and catalyst (strong base acid acceptor), can be done either in one step or via RFCH=CHCH2OH; however, dehydrohalogenation may also give the epoxide, and reduction in this case leads to the secondary alcohol, RFCH2CH(CH3)OH.By contrast, reduction of RFCH2CHICH2OAc by tributyltin hydride or with hydrogen over palladium (diethylamine acid acceptor) goes smoothly.Zinc and acid reduction of RFCH2CHICH2OAc gives elimination to RFCH2CH=CH2; even RFCH=CICH2OH gives RFCH=C=CH2 besides RFCH=CHCH2OH.RFCH=CICH2CH2OH, however, with zinc and acid is reduced cleanly to RFCH=CHCH2CH2OH.
