Recognition of cyclic, acyclic, exocyclic, and spiro Acetals via structurally diagnostic ion/molecule reactions with the (CH3)(2)N-C+=O acylium ion

Recognition of cyclic, acyclic, exocyclic, and spiro Acetals via structurally diagnostic ion/molecule reactions with the (CH3)(2)N-C+=O acylium ion

Author Benassi, Mario Google Scholar
Moraes, Luiz Alberto B. Google Scholar
Cabrini, Liliane G. Google Scholar
Dias, Luiz Carlos Google Scholar
Aguilar, Andrea M. Autor UNIFESP Google Scholar
Romeiro, Gilberto A. Google Scholar
Eberlin, Livia S. Google Scholar
Eberlin, Marcos N. Google Scholar
Institution Universidade Estadual de Campinas (UNICAMP)
Universidade de São Paulo (USP)
Universidade Federal de São Paulo (UNIFESP)
Universidade Federal Fluminense (UFF)
Abstract Reactions of the model acylium ion (CH3)(2)N-C+=O with acyclic, exocyclic, and Spiro acetals of the general formula (RO)-O-1-(CRR4)-R-3-OR2-upole mass spectrometry. Characteristic intrinsic reactivities were observed for each of these classes of acetals. the two most Characteristic intrinsic reactivities were observed for each of these classes of acetals. the two most common reactions observed were hydride and alkoxy anion [(RO-)-O-1 and (RO-)-O-2] abstraction. Other specific reactions were also observed: (a) a secondary polar [4(+) + 2] cycloaddition for acetals bearing alpha,beta-unsaturated R-3 or R-4 substituents and (b) OH- abstraction for exocyclic and spiro acetals. These structurally diagnostic reactions, in conjunction with others observed previously for cyclic acetals, are shown to reveal the class of the acetal molecule and its ring type and substituents and to permit their recognition and distinction from other classes of isomeric molecules.
Language English
Date 2008-07-18
Published in Journal of Organic Chemistry. Washington: Amer Chemical Soc, v. 73, n. 14, p. 5549-5557, 2008.
ISSN 0022-3263 (Sherpa/Romeo, impact factor)
Publisher Amer Chemical Soc
Extent 5549-5557
Origin http://dx.doi.org/10.1021/jo8008269
Access rights Closed access
Type Article
Web of Science ID WOS:000257543100043
URI http://repositorio.unifesp.br/handle/11600/30802

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