Synthesis and photochemical reaction of diels-alder adduct of phosphole oxide and cyclopentadiene

✍ Scribed by Hideo Tomioka; Shinichi Miura; Yasuji Izawa

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 212 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)86268-1

✦ Synopsis

Irradiation of 1-phenylphosphole oxide-cyclopentadiene adduct gave a caged product, whereas similar irradiation of 1,2,5-triphenylphosphole oxidecyclopentadiene adduct afforded a cleavaged product. Previous studies 2) from this laboratory showed that the Diels-Alder dimer of 1-phenylphosphole oxide (1) underwent an interesting photochemical conversion. Thus, direct irradiation of the dimer (1) resulted in an efficient extrusion of Ph-P=O bridge, while the sensitized irradiation produced a caged product (2) as a result of intramolecular [2 + 21 cycloaddition. The former reaction is a useful method to generate the reactive phosphorus intermediate, 1,3) analogous to carbene and nitrene, and has recently been employed 4) to build a new phosphorus heterocycles. The latter, on the other hand, has recieved much attentions as one of efficient energy storage system. Thus, as an extension of this study, we have prepared the Diels-Alder adducts of phosphole oxide with cyclopentadiene and