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Detection and Mechanistic Implication of a Dynamic Equilibrium in Some Novel Spiro-heterocyclic Systems by Alex I.D. Alanine; Colin W.G. Fishwick; Csaba Szantay Jr. is a Chemistry article available to read on EtoBox.

What is Detection and Mechanistic Implication of a Dynamic Equilibrium in Some Novel Spiro-heterocyclic Systems about?

Evidence is presented based upon NMR analysis for a novel dynamic equilibrium in a number of Spiro-heterocyck compounds which involves inversion at only one of two asymmetric centres present in each system. We have repotted2 previously that the novel spirocyclic systems 3 and 4 (n=l , 2) are obtained from the 1,3-dipolar cycloadditions of imidate methylides 2, which are generated via desilylation of salts 1 (Scheme 1). It was found that the reaction of methyl methacrylate with azomethine ylide 2, n=l, yielded only 3a (RI = Me, R\* = COOMe); in every other case only regioisomers of type 4 were isolable. These regioisomers were also found to exist as mixtures of diastereoisomers, which was evident by the presence of strong saturation transfer effects that relate analogous protons of the epimers in the one-dimensional t H-'H NOE difference experiments,s are in dynamic equilibrium involving inversion at only one of the two asymmetric centres present. 1 2 scheme 1 Me Me 3a R1=Me, R2=C02Me 4 a

Who reads Detection and Mechanistic Implication of a Dynamic Equilibrium in Some Novel Spiro-heterocyclic Systems?

Author

Alex I.D. Alanine; Colin W.G. Fishwick; Csaba Szantay Jr.

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

1989

Language

EN

Field

Chemistry (Physical Sciences)