Bulletin of the Chemical Society of Japan p. 1151 - 1158 (1981)
Update date:2022-09-26
Topics:
Yanagida, Shozo
Noji, Yukihiro
Okahara, Mitsuo
Perfluoro-2-methyl-2-pentene (PMP) reacts with carboxylic acids, alcohols, and 2-pyridone, giving Michael-type addition products, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3-acyloxypentane, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3-alkoxypentane, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3(2-pyridyloxy)pentane, respectively, in good yields.In the presence of bases, carboxylic acids give acid fluorides, 1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethyl-3-pentanone, and 1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethyl-3-acyloxy-2-pentene (4), the yields changing with base, solvent, phase-transfer catalyst, and their combination.In the presence of triethylamine, fluorination occurs exclusively, producing acid fluorides in good yields.Alcohols and 2-pyridone are converted into alkyl fluorides and 2-fluoropyridine, respectively, with use of triethylamine as a base with an aprotic solvent.The reaction of PMP with 4-pyridone and 6-chloro-2-ethyl-5-methyl-4(3H)-pyrimidone were also examined.The fluorination reactions were rationalized by preferential replacement of the vinylic fluorine of PMP and a good leaving function of the perfluoro enol group of the intermediates such as 4.
View Morewebsite:http://www.simagchem.com
Contact:+86-592-2680277
Address:21/F Hualong Office Building,No.6 Hubin East Road, Xiamen,China
Contact:0091-265-2313036
Address:311, ATLANTIS HEIGHTS SARABHAI MAIN ROAD,VADIWADI ,VADODARA
Hangzhou Hysen Pharma co.,Ltd.
website:http://www.hysenpharma.cn/
Contact:0086-571-88298791
Address:#701,Gudun Road Hangzhou
Contact:86-21-57725962
Address:shanghai
TIANJIN ZHONGXIN CHEMTECH CO.,LTD.
Contact:86-022-89880739
Address:10B, Pan China International Center, No. 931 YingKou Road, TangGu, Tianjin, China, 300451
Doi:10.1039/b600032k
(2006)Doi:10.1016/S0040-4020(01)97679-3
(1981)Doi:10.1021/jacs.9b07763
(2019)Doi:10.1016/S0022-328X(00)82969-1
(1981)Doi:10.1248/cpb.33.1116
(1985)Doi:10.1016/j.bmcl.2011.10.022
(2011)