Record number :
1884549
Title of article :
Photochemical transformation of a 1,2-dihydropyridin-3-one: an original tandem retro-[4+2]/[2+2] cycloaddition process
Author/Authors :
Aitken، نويسنده , , David J. and Frongia، نويسنده , , Angelo and Gaucher، نويسنده , , Xavier and Ollivier، نويسنده , , Jean and Rafique، نويسنده , , Hummera and Sambiagio، نويسنده , , Carlo and Secci، نويسنده , , Francesco، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2013
Pages :
3
From page :
2825
To page :
2827
Abstract :
The UV irradiation of N-benzyl-2-phenyl-1,2-dihydropyridin-3-one furnished trans-1-benzyl-4-phenyl-3-vinylazetidin-2-one, a structural isomer, as the main product. A novel tandem mechanism involving a [4+2] photocycloreversion followed by a Staudinger cycloaddition reaction is proposed, and is supported with the trapping of the purported vinylketene intermediate by other imines. This process predominates in the presence of ethylene, precluding the formation of an intermolecular [2+2] cyclobutane adduct.
Keywords :
Dihydropyridinones , photochemistry , cycloaddition , Staudinger reaction , ?-Lactams
Journal title :
Tetrahedron Letters
Serial Year :
2013
Link To Document :
بازگشت