Investigations into the role of ion pairing in reactions of heteroatom-substituted cyclic oxocarbenium ions
- PMID: 15760163
- DOI: 10.1021/ol0500620
Investigations into the role of ion pairing in reactions of heteroatom-substituted cyclic oxocarbenium ions
Abstract
[reaction: see text] The O-to-C rearrangement of vinyl acetals is used to demonstrate that tight ion pairing is not involved in the stereoselective nucleophilic addition reactions of alkoxy-substituted cyclic oxocarbenium ions.
Similar articles
-
Using stereoelectronic effects to explain selective reactions of 4-substituted five-membered ring oxocarbenium ions.Org Lett. 2004 Jun 10;6(12):2063-6. doi: 10.1021/ol0492647. Org Lett. 2004. PMID: 15176819
-
Using nucleophilic substitution reactions to understand how a remote alkyl or alkoxy substituent influences the conformation of eight-membered ring oxocarbenium ions.Org Lett. 2004 Dec 9;6(25):4739-41. doi: 10.1021/ol047998d. Org Lett. 2004. PMID: 15575674
-
Nucleophilic additions of trimethylsilyl cyanide to cyclic oxocarbenium ions: evidence for the loss of stereoselectivity at the limits of diffusion control.J Am Chem Soc. 2006 Jul 5;128(26):8671-7. doi: 10.1021/ja061110u. J Am Chem Soc. 2006. PMID: 16802834
-
Fischer carbene complexes: beautiful playgrounds to study single electron transfer (SET) reactions.Chemistry. 2007;13(3):736-44. doi: 10.1002/chem.200601470. Chemistry. 2007. PMID: 17171739 Review.
-
Coinage metal catalyzed C-H bond functionalization of hydrocarbons.Chem Rev. 2008 Aug;108(8):3379-94. doi: 10.1021/cr078364y. Chem Rev. 2008. PMID: 18698739 Review. No abstract available.
Cited by
-
Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond.Chem Sci. 2020 Sep 7;11(37):10101-10106. doi: 10.1039/d0sc04340k. Chem Sci. 2020. PMID: 34094271 Free PMC article.
-
Traceless chiral auxiliaries for the allene ether Nazarov cyclization.J Org Chem. 2008 Nov 7;73(21):8133-41. doi: 10.1021/jo801503c. Epub 2008 Sep 23. J Org Chem. 2008. PMID: 18808186 Free PMC article.
-
Surveying approaches to the formation of carbon-carbon bonds between a pyran and an adjacent ring.Tetrahedron. 2006 May 1;62(18):4573-4583. doi: 10.1016/j.tet.2006.02.042. Tetrahedron. 2006. PMID: 17710219 Free PMC article.
-
Bromine-Promoted Glycosidation of Conformationally Superarmed Thioglycosides.Chemistry. 2019 Sep 12;25(51):11831-11836. doi: 10.1002/chem.201901969. Epub 2019 Aug 20. Chemistry. 2019. PMID: 31286579 Free PMC article.
-
Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals.J Am Chem Soc. 2011 May 25;133(20):7916-25. doi: 10.1021/ja201249c. Epub 2011 May 3. J Am Chem Soc. 2011. PMID: 21539313 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources