Formation of cyclic nitrone from nitrite of fused five-membered ring alcohol by photochemical rearrangement (1)

✍ Scribed by Hiroshi Suginome; Norio Sato; Tadashi Masamune

• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 216 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99761-2

✦ Synopsis

The photochemical transformation of nitrite esters of fused 5-membered ring alcohols usually leads to the formation of cyclic hydroxamic acids (2). We wish to-report that irradiation of the nitrite Ib of a fused cyclopentanol induces extensive reorganization of the molecule and leads to the formation of a novel cyclic nitrone II with an excellent yield. The nitrite Ib, m-p. 179-182O, was prepared from jervine via 7 steps (3). Photolysis of Ib in toluene for 3 hr as described in the previous paper (4) produced II as virtually the sole product (59%). Structure II of the photoproduct was deduced on the basis of the spectroscopic, chemical and photochemical evidence and the consideration of the mode of the formation.