Substituent effects on 1,3-dipolar cycloadditions to some 1,1-diphenyl-2-aza-1,3-butadiene derivatives.

✍ Scribed by Cesarino Balsamini; Annalida Bedini; Gilberto Spadoni; Marina Burdisso; Anna Maria Capelli

• Book ID: 104205301
• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 737 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)90397-7

✦ Synopsis

Key twxd.% I,3-Dipolar cycloaddidons;

2-Asa-1,3-butadienesi 2,3-Dehydroamino acIcIs; Sfteselectivity.

Absawt : Tbe reactivfty and in partJcular the siteselectlvity of [3+2] electrocyclic additions to l,l-dJpJw?nyl-2-aza -1,3-butadknes, substftuted or not on tie term&M carbon wltb metiyJ and pbenyl, and wJth a 3-carbometboxyl group, J&we been Lavestfgated wit& the 1,3-dJJx&u reagents 4-nitrobenzonitie oxJde and diazomethane.

Tbe role of the 3carbometboxy substituent in de termMng the sfteseJectivJty observed In these reactions is discussed in n?JatJon to experJmentaJ resdts and to confonna~fonaJ models of some of the tested 2-azadiene dJpoJ_pMJes caJcuJat&l on AM1 bases.