Synthesis of β-keto- and vinyl phosphonates = 베타 케토 및 비닐 포스포네이트의 합성

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A convienient synthetic methods for the preparation of a variety of $\beta$-keto phosphonates and vinyl phosphonates were studied. Sodium diethyl phosphite were reacted with a wide range of epoxy sulfones to give $\beta$-keto phosphonates. In this reaction aryl epoxy sulfones appeared to be the synthetic equivalent for ketone equivalents with $\alpha$-cation reactivity. Unexpectedly, when 2-phenyl-2-(phenylsulfonyl)-1,2-epoxyethane was reacted, trans-styryl phosphonate was produced in about half yield. It is supposed that initially formed 1-formyl benzyl phosphonate reacts with additional sodium diethylphosphite. When 1-formyl benzyl phosphonate was reacted with dialkyl phosphite sodium salt in tetrahydrofuran at room temperature, corresponding dialkyl phenyl alkenephosphonates were produced in high yield. In this reaction, 1-formyl benzyl phosphonate could be used as trans styryl cation equivalent. However, when $\alpha$-formyl benzyl phosphonate which do not have $\alpha$-electron withdrawing group was reacted, alkenyl phosphonate did not form. Furthermore, from the reaction of 1-phenyl-2-diethyl phosphonyl ethanone with diethyl phosphite sodium salt, 2-phenyl ethene phosphonate were obtained with 2-hydroxy-2-phenyl ethane phosphonate.
Advisors
Oh, Dong-Young오동영
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1994
Identifier
68931/325007 / 000895013
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1994.2, [ v, 104 p. ]

URI
http://hdl.handle.net/10203/31389
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=68931&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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