Synthesis of alkyl perfluoroalkyl ketones reactions of allyl perfluoroalkanoates with acyl chlorides in the presence of palladium(0)

✍ Scribed by Qing-Yun Chen; Jian-Guo Chen

• Publisher: Elsevier Science
• Year: 1989
• Tongue: English
• Weight: 674 KB
• Volume: 42
• Category: Article
• ISSN: 0022-1139
• DOI: 10.1016/s0022-1139(00)83929-9

✦ Synopsis

The reactions of fluorocarbanions derived from palladium(O) mediated decomposition of ally1 esters of fluoroalkylether acids, RfC02CH2CH=CH2(Rf=C3F70[CF(CF3)CF20]nCF(CF3), n=O,l), with acyl chlorides yielded en01 esters of hemifluorinated ketones, RR'C=C(Rf)OCOCHRR', n=O, 4; n=l, 5, plus a very small amOunt of the ketones RfCOCHRR', n=O, 6; n=l, 7, or ally1 ketones, RfCOCHRCH2CH=CH2, 8, with a small amount of diallyl ketones, RfCOCR(CH2CH'CH2)2, 9, depending on the reaction conditions employed. Esters 4, 5 could be converted to ketones 6, 7 in excellent yields with concentrated sulfuric acid.