Strength in Numbers

A timely NSF grant helps women scientists discover the value of networking and mentoring to their careers -- and their lives

Technology for the Organic Chemist: Three Exploratory Modules

The ability to use computer-based technology is an essential skill set for students majoring in chemistry. This exercise details the introduction of appropriate uses for this technology in the organic chemistry series. The incorporation of chemically appropriate online resources (module 1), scientific databases (module 2), and the use of a chemical drawing program (module 3) are detailed here

Projects That Assist with Content in a Traditional Organic Chemistry Course

Projects that engage undergraduate students in content-based courses, such as organic chemistry, must relate to the material and provide useful tools for the divergent needs of the students. There are few examples of these types of projects in the literature. Herein, we describe two projects, the reaction notebook and the end-of-semester synthesis activity. Each project is designed to stimulate student ownership of the material and leads to engagement with the content of the course

A Flexible Solvolysis Experiment for the Undergraduate Organic Laboratory

A simple SN1 reaction is presented that uses bromotriphenylmethane and a range of oxygen-based nucleophiles including water and various alcohols. This procedure represents a process that affords easy isolation of solid products. Typical student yields ranged from 17–128% with the average yield of 50%. Students obtained products with a melting point range of 140 to 164 °C. This procedure offers multiple ways to adapt this experiment from a straight solvolysis reaction to a discovery-based experiment that explores the effect of nucleophile (for a more advanced group) or the method of product isolation

Unexpected Syntheses of seco-Cyclopropyltetrahydroquinolines From a Radical 5-Exo-Trig Cyclization Reaction: Analogs of CC-1065 and the Duocarmycins

Abstract: Analogs of the seco-cyclopyrroloindoline (seco-CPI), the DNA alkylation pharmacophore of CC-1065 and the duocarmycins, can be prepared through a 5-exo-trig radical cyclization of a free radical and a 3-chloro-2-allylic moiety. This manuscript reports an unexpected discovery that, depending on the structure and stability of the free radical, the cyclization process leads to the production of an appreciable amount of secocyclopropyltetrahydroquinolines 7a-d along with the seco-cyclopropoyltetrahydroindoline products (6a-e). For instance, free radical reaction of the bromoallylic chloride 5a produced an equal amount of 6-benzyloxy-N-t-butoxycarbonyl-3-(chloromethyl)furano[e]indoline (6a), and 7-benzyloxy-N-t-butoxycarbonyl-3-chloro-1,2,3,4-tetrahydrofurano[f]quinoline (7a). Three other examples that produced mixtures of indoline and quinoline products are provided. In only one of the examples reported in this manuscript, the 6-benzyloxy-N-t-butoxycarbonyl-3-(chloromethyl)benzo[e]indoline, was a seco-CBI precursor 6e formed exclusively, consistent with literature precedents

Unexpected Syntheses of \u3cem\u3eseco\u3c/em\u3e-Cyclopropyltetrahydroquinolines From a Radical 5-\u3cem\u3eExo-Trig\u3c/em\u3e Cyclization Reaction: Analogs of CC-1065 and the Duocarmycins

Analogs of the seco-cyclopyrroloindoline (seco-CPI), the DNA alkylation pharmacophore of CC-1065 and the duocarmycins, can be prepared through a 5-exo-trig radical cyclization of a free radical and a 3-chloro-2-allylic moiety. This manuscript reports an unexpected discovery that, depending on the structure and stability of the free radical, the cyclization process leads to the production of an appreciable amount of seco- cyclopropyltetrahydroquinolines 7a-d along with the seco-cyclopropoyltetra- hydroindoline products (6a-e). For instance, free radical reaction of the bromoallylic chloride 5a produced an equal amount of 6-benzyloxy-N-t-butoxycarbonyl-3- (chloromethyl)furanoe]indoline (6a), and 7-benzyloxy-N-t-butoxycarbonyl-3-chloro- 1,2,3,4-tetrahydrofuranof]quinoline (7a). Three other examples that produced mixtures of indoline and quinoline products are provided. In only one of the examples reported in this manuscript, the 6-benzyloxy-N-t-butoxycarbonyl-3-(chloromethyl)benzoe]indoline, was a seco-CBI precursor 6e formed exclusively, consistent with literature precedents