RUI: Electrophilic Reactions of Fluorosubstituted Alkenes with Chlorosulfonyl Isocyanate and some other Electrophiles

有了这个更新奖，化学结构、动力学和机制项目将继续支持洛马拿撒勒学院的Dale F. Shellhamer教授对氟取代烯烃的亲电反应的研究。这些研究将集中于氯磺酰异氰酸酯与单氟烯烃反应生成氟取代β -内酰胺的机理。将采用动力学测量、产品研究和计算化学来了解导致氯磺酰异氰酸酯的添加从大多数氟烯烃的明显一步过程转变为碳氢化合物和一些氟碳烯烃的分步过程的因素。虽然非氟内酰胺和其他含氟化合物通常是重要的药物制剂，但氟内酰胺在很大程度上尚未开发，应该证明是非常有趣的药用化合物。这个项目的一个重要方面将是本科生作为研究人员参与项目的各个方面。学生将获得有机合成、核磁共振光谱、质谱、振动光谱和计算化学方面的专业知识。谢尔哈默教授在让本科生参与研究并激励他们继续深造化学和医学方面有着出色的记录。

With this Renewal Award, the Chemical Structure, Dynamics, and Mechanisms Program continues to support Professor Dale F. Shellhamer of Point Loma Nazarene College in his investigations of electrophilic reactions of fluorosubstituted alkenes. These studies will be focused on the mechanism of the reaction of chlorosulfonyl isocyanate with monofluoroalkenes to generate fluoro substituted beta-lactams. Kinetic measurements, product studies and computational chemistry will be employed to gain an understanding of the factors that cause additions of chlorosulfonyl isocyanate to change from an apparent one-step process with most fluoroalkenes to a step-wise process with hydrocarbons and some fluorocarbon alkenes. Although non-fluorinated lactams and other fluorinated compounds are often important pharmaceutical agents, fluorinated lactams are largely unexplored and should prove to be very interesting medicinal compounds.An important aspect of this project will be the involvement of undergraduate students as researchers in all facets of the project. Students will gain expertise in organic synthesis, NMR spectroscopy, mass spectrometry, vibrational spectroscopy and computational chemistry. Professor Shellhamer has an excellent record of involving undergraduates in research and inspiring them to go on to advanced study in chemistry and medicine.