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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 12
BKCSDE 28(12)
December 20, 2007 

Synthesis of 3,3-Difluoro-2-pyrrolidone Derivatives
Sung-Kwan Kim, Zhi-Feng Xie, Chang-Soo Jun, Tae-Ho Kwon, Soung-Ryual Ryu, Kyu-Yun Chai*
3,3-Difluoro-2-pyrrolidone, α,α-Difluoro-γ-lactam, Difluoromethylene group
Introduction of a difluoromethylene group into organic compounds has been observed to impart them with positive properties, as viewed by a wide range of industries. Here, synthesis of 3,3-difluoro-2-pyrrolidone derivatives (7) was accomplished by the reaction of ethyl 2,2-difluoro-4-iodo-4-(trimethylsilyl) butanolate (4) with primary amines followed by desilylation. The key intermediate (4) was prepared from the addition reaction of trimethylvinylsilane (3) to ethyl difluoroiodoacetate (2) in the presence of Cu(0). Ethyl difluoroiodoacetate (2) was prepared starting from ethyl bromodifluoroacetate (1) via Reformatsky-type reaction.
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