Unsaturated Sulfones in Organic Synthesis (Chemistry)

有机合成中的不饱和砜（化学）

• 批准号: 8800008
• 负责人: Albert Padwa
• 金额: $ 24.51万
• 依托单位: Emory University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1988
• 资助国家: 美国
• 起止时间: 1988-06-01 至 1991-08-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=8800008&HistoricalAwards=false
• 关键词: Unsaturated; Sulfones; Organic; Synthesis; Chemistry

This research will be supported by the Organic and Macromolecular Chemistry Program. The research will develop the chemistry of a class of sulfur containing molecules as a new synthetic pathway to the synthesis of molecules containing polycyclic systems. The development of these reactions will result in new methods for the preparation of the complex materials needed in medicine and agriculture. The chief objective of the research on the chemistry of unsaturated sulfones is to open up new synthetic methods for the preparation of unusual polycyclic ring systems. It is envisioned adding a variety of functionalized nucleophiles to phenylsulfonylallene followed by a subsequent base induced cyclization so as to prepare novel ring systems which could be of considerable use in organic synthesis. Substituted thiophenyl allyl sulfones undergo a 1,3-allylic sulfonyl shift and this process will be utilized within a metallation-alkylation sequence to prepare a variety of sulfonyl functionalized substrates. Other studies will deal with the recently uncovered ı3+2!-anionic cyclization of phenylsulfonyl-allene with methyl vinyl ketone. Since the ı3+2!-anionic cycloaddition strategy has not been investigated for the general synthesis of cyclopentenes, the cyclization reaction with a number of activated allenes and alkenes will be studied. Plans also include a study of the chemistry of diazafulvene, which it is believed can be generated as a transient species from the cycloadduct derived from diazomethane and phenylsulfonylallene. Another objective of the investigation will be to develop the chemistry of sulfonyl substituted cyclopropenes as reagents for the synthesis of some novel polycyclic ring systems.

这项研究将得到有机和 高分子化学计划。 这项研究将发展 化学的一类含硫分子作为一个 新的合成途径来合成含有 多环系统 这些反应的发展将 为制备该配合物提供了新的方法， 医药和农业所需的材料。 化学研究的主要目标是 不饱和砜是开辟新的合成方法， 不寻常的多环体系的制备。 是 设想将各种官能化亲核试剂加入到 苯磺酰基丙二烯，随后是碱诱导的 环化以制备新的环体系， 在有机合成中有相当大的用途。 取代 噻吩基烯丙基砜发生1，3-烯丙基磺酰基位移 这一过程将在一个 金属化-烷基化顺序来制备各种 磺酰基官能化的基底。 其他研究将涉及 最近发现的3 +2！阴离子环化 苯磺酰基-丙二烯与甲基乙烯基酮。 以来 ı3+2！-阴离子环加成策略尚未研究 对于环戊烯的一般合成， 与许多活化的联烯和烯烃的反应将是 研究了 计划还包括研究 二氮富烯，它被认为可以作为一种 来自衍生自以下的环加合物的瞬态物质： 重氮甲烷和苯磺酰基丙二烯。 的另一个目的 研究将是发展磺酰基的化学 取代的环丙烯作为合成某些 新颖的多环体系。