Substituent Effects on Regioselectivity in the Photorearrangement of a Few Naphthobarrelenes

✍ Scribed by Meledathu C Sajimon; Danaboyina Ramaiah; S Ajaya Kumar; Nigam P Rath; Manapurathu V George

• Book ID: 104202802
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 151 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00450-6

✦ Synopsis

AbstractÐThe photorearrangement of a few 9,10-disubstituted-naphthobarrelenes to the corresponding naphthosemibullvalenes has been examined. It was observed that the regioselectivity in these photoisomerizations depends on the relative stabilities of the diradical intermediates. AM1 semi-empirical calculations are in support of this view. Thermal transformation of the naphthosemibullvalenes gave the corresponding water added naphthopentalenofurans, in nearly quantitative yields.