Aromatic 4-Tetrahydropyranyl and 4-Quinuclidinyl Cations. Linking Prins with Cope and Grob
- 11 April 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (18) , 4960-4961
- https://doi.org/10.1021/ja025902+
Abstract
The chair 4-tetrahydropyranyl cation and the 4-quinuclidinyl cation are shown to be energy minima and to be delocalized, with exceptionally long CH2CH2 bonds, according to B3LYP/6-31G* calculations; the implications for Prins cyclizations, Cope rearrangements, and Grob fragmentations are discussed.Keywords
This publication has 15 references indexed in Scilit:
- Stereocontrolled synthesis of 2,4,5-trisubstituted tetrahydropyransChemical Communications, 2001
- CryptoCope Rearrangement of 1,3-Dicyano-5-phenyl-4,4-d2-hexa-2,5-diene. Chameleonic or Centauric?Journal of the American Chemical Society, 1999
- A Becke3LYP/6-31G* Study of the Cope Rearrangements of Substituted 1,5-Hexadienes Provides Computational Evidence for a Chameleonic Transition StateJournal of the American Chemical Society, 1999
- Aromaticity of pericyclic reaction transition structures: magnetic evidenceJournal of Physical Organic Chemistry, 1998
- Nucleus-Independent Chemical Shifts: A Simple and Efficient Aromaticity ProbeJournal of the American Chemical Society, 1996
- The Prins and Carbonyl Ene ReactionsPublished by Elsevier ,1991
- Donor‐Acceptor‐Substituted Cyclic π‐Electron Systems—Probes for Theories and Building Blocks for New MaterialsAngewandte Chemie International Edition in English, 1988
- Die nucleofuge Aktivität von Substituenten am Brückenkopf von Bicyclo[2.2.2]octan und Chinuclidin DaskOTs/kBr-Verhältnis als mechanistisches Kriterium. Fragmentierungsreaktionen, 24. MitteilungHelvetica Chimica Acta, 1970
- Transannular Dipolar and Neighboring Group Effects in Simple Oxygen Heterocycles on Rates of Solvolysis of ArenesulfonatesJournal of the American Chemical Society, 1969
- Mechanisms and Stereochemistry of Heterolytic FragmentationAngewandte Chemie International Edition in English, 1969