合成可分离的二二 (α-dithiolactone) 从基S-氧化物
Kentaro Okuma1, Toshiyuki Shigetomi, Yoshinori Nibu
1Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan. kokuma@fukuoka-u.ac.jp
Journal of the American Chemical Society
|August 5, 2004
概括
研究人员通过使用Lawesson试剂和di-tert-butyl thioketene S-oxide合成了3,3-di-tert-butylthiirane-2-thione. 进一步的氧化产生了相应的S-氧化物,详细说明了氨酸-氨酸的反应性.
科学领域:
- 有机化学 有机化学
- 硫化学 硫的化学
背景情况:
- 基及其衍生物是反应性中间体.
- 硫衍生物是含硫的异环,具有独特的化学性质.
研究的目的:
- 为了合成新型烯衍生物.
- 为了研究二二和其S-氧化物的反应性.
主要方法:
- 用劳埃森试剂对二特尔-丁 thioketene S-oxide 的反应.
- 使用m-二酸氧化得到的二二.
主要成果:
- 在88%的产量中成功合成了3,3-di-tert-butylthiirane-2-thione.
- 通过氧化制备3,3-di-tert-butylthiirane-2-thione S-氧化物.
- 反应产品的表征和硫二化学的描述.
结论:
- 迪特尔-乙基 thioketene S-oxide 是一种可行的 thiirane-2-thione 合成的前体.
- 硫-2-可以被选择性氧化到它的S-氧化物.
- 这项研究扩展了已知的兰-氨酸化合物的反应.
相关概念视频
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Oxidative Cleavage of Alkenes: Ozonolysis
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Oxidation of Alcohols
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
The process of oxidation in a chemical reaction is observed in any of the three forms:
Preparation and Reactions of Thiols
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
Preparation and Reactions of Sulfides
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Aldol Condensation with β-Diesters: Knoevenagel Condensation
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.


