Photochemical transformation of a 1,2-dihydropyridin-3-one: an original tandem retro-[4+2]/[2+2] cycloaddition process

被引：1
作者：
Aitken, David J. [1 ]
Frongia, Angelo [2 ]
Gaucher, Xavier [1 ]
Ollivier, Jean [1 ]
Rafique, Hummera [1 ]
Sambiagio, Carlo [1 ,2 ]
Secci, Francesco [2 ]
机构：
[1] Univ Paris 11, ICMMO CNRS, UMR 8182, F-91405 Orsay, France
[2] Univ Cagliari, Dipartimento Sci Chim, I-09042 Cagliari, Italy
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 22期
关键词：
Dihydropyridinones; Photochemistry; Cycloaddition; Staudinger reaction; beta-Lactams; PHOTOISOMERIZATION; PHOTOADDITION; INTERMEDIATE; IMINES;
D O I：
10.1016/j.tetlet.2013.03.081
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2825 / 2827
页数：3
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