Intramolecular nucleophile-induced photorearrangements and silene formation from an o-(methoxymethyl)phenylsilacyclobutane

J Am Chem Soc. 2003 Jul 9;125(27):8096-7. doi: 10.1021/ja035283k.

Abstract

Direct photolysis of 1-(o-(methoxymethyl)phenyl)-1-phenylsilacyclobutane yields three isomeric products attributed to intramolecular trapping of an initially formed silicon-carbon biradical intermediate by migration of the benzylic methoxy group to silicon, along with the (expected) intramolecularly ether-stabilized silene due to formal [2 + 2]-cycloreversion.