Reference : Cycloadditions of diazoesters to α,β-unsaturated aldehydes
Scientific journals : Article
Physical, chemical, mathematical & earth Sciences : Chemistry
http://hdl.handle.net/2268/236096
Cycloadditions of diazoesters to α,β-unsaturated aldehydes
English
Noels, Alfred mailto [Université de Liège - ULiège > > Relations académiques et scientifiques (Sciences) >]
Braham, J. N. [Université de Liège - ULiège > >]
Hubert, André J. [> >]
Teyssie, Philippe [Université de Liège - ULiège > > Relations académiques et scientifiques (Sciences) >]
1978
Tetrahedron
Elsevier
34
23
3495-3497
Yes (verified by ORBi)
International
00404020
United Kingdom
[en] The reaction of α,β-unsturated aldehydes with diazoesters primarily gives unstable 1,3-dipolar adducts (1-pyrazolines) which evolve according to their substitution pattern: whenever there is a proton geminal to the formyl group, conjugation with the latter is highly favoured, yielding 3-formyl-2-pyrazolines which subsequently polymerize. On the other hand, if no proton is available for conjugation with the formyl group, two competitive reactions take place: tautomerisation into an ester conjugated pyrazoline and loss of nitrogen with formation of cyclopropanes, the latter reactionnal pathway being favoured with electronwithdrawing substituents. © 1978.
Researchers ; Professionals
http://hdl.handle.net/2268/236096
10.1016/0040-4020(78)80237-3

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