A photochemical preparation of indoles: An organic chemistry experiment

Abstract

A Photochemical Preparation of Indoles An organic chemistry experimentThe chemical literature is filled with a variety of organic laboratory photoreactions, which provide novel heterocycles, molecules of theoretical interest, and pharmaceutically valuable, naturally occurring materials. In industry, perhaps the most impressive photochemical process to date is the photooximation of cyclohexane, which produces f-caprolactam (the precursor to Nylon-6) on a 150,000 ton per year scale (7 ). The process was developed by Toyo Rayon of Japan and what is truly remarkable is that the photoreaction proceeds with a quantum yield of less than unity and the product sells for $l-$2/kg. Despite these documented achievements, a search through the many popular organic laboratory textbooks reveals that at best, a single photochemical experiment is included. Almost without exception, the experiment involves the sunlight initiated photoreduction of benzophenone to benzophenol. While the experiment is certainly convenient, it, unfortunately, demonstrates little of the synthetic value of modern organic