THERMALLY STABLE SULFENIC ACID: (3R,4R)-1-(TERT-BUTYLDIMETHYLSILYL)-3-PHTHALIMIDO-2-OXO-AZETIDINE-4-SULFENIC ACID

THERMALLY STABLE SULFENIC ACID: (3R,4R)-1-(TERT-BUTYLDIMETHYLSILYL)-3-PHTHALIMIDO-2-OXO-AZETIDINE-4-SULFENIC ACID
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DOI:
10.1002/chin.198228177
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发表时间:
1982-02
期刊:
ChemInform
影响因子:
--
通讯作者:
M. Bachi;A. Gross
M. Bachi;A. Gross
中科院分区:
其他
文献类型:
--
作者:
M. Bachi;A. Gross

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除了少数由蒽醌 1 和尿酰基 2 衍生的次磺酸通过分子内氢键稳定外,次磺酸一直被认为是高反应性和难以捉摸的化合物。核磁共振和红外光谱数据及其原位化学衍生化提供了二叔丁基亚砜热解过程中叔丁基磺酸形成的证据。 3 一些脂肪族和芳香族次磺酸是通过亚砜的快速真空热解产生的,并在 196℃ 下分离,但在升温至环境温度时自发自缩合成相应的硫代亚磺酸盐。 4 据报道,各种次磺酸在各种化学反应 5 和生物转化反应中作为活性瞬态物质。
Except for a few sulfenic acids deriving from anthra-quinone1 and from uracyl, 2 which are stabilized by intra-molecular hydrogen bonding, sulfenic acids havebeen considered as highly reactiveand elusive compounds. Evidence for the formationof tert-butylsulfenic acid in the thermolysis ofdi-tert-butyl sulfoxide was provided by NMR and IR spectral data and by its chemical derivati-zation in situ. 3 Some aliphatic and aromatic sulfenic acids were produced by flash vacuum pyrolysis of sufoxides and isolated at-196 C but underwent a spontaneous self-condensation to the corresponding thiolsulfinate on warming to ambient temperature. 4 Various sulfenicacids have been reported as reactive transient species in a wide variety of chemicalreactions5 and biologicaltransforma-