dc.contributor.author | Taboada, Rosa | |
dc.contributor.author | Ordonio, Grace G | |
dc.contributor.author | Ndakala, Albert J | |
dc.contributor.author | Howell, Amy R | |
dc.date.accessioned | 2013-06-17T14:02:37Z | |
dc.date.available | 2013-06-17T14:02:37Z | |
dc.date.issued | 2003 | |
dc.identifier.citation | J. Org. Chem., 2003, 68 (4), pp 1480–1488 | en |
dc.identifier.uri | http://pubs.acs.org/doi/abs/10.1021/jo0206465 | |
dc.identifier.uri | http://erepository.uonbi.ac.ke:8080/xmlui/handle/123456789/35052 | |
dc.description.abstract | 1,5-Dioxaspiro[3.2]hexanes undergo ring-opening reactions with many heteroatom nucleophiles to provide α-substituted-β‘-hydroxy ketones. However, certain Lewis acidic nucleophiles provide 2,2-disubstituted oxetanes. Herein, the results of reactions of 3-phenyl-1,5-dioxaspiro[3.2]hexane with a variety of nitrogen-containing heteroaromatic bases are reported. There appears to be a correlation between the pKa of the nucleophile and the reaction outcome with more acidic nucleophiles providing 2,2-disubstituted oxetanes. Moreover, the mode of ring opening can be directed toward the substituted oxetane by the addition of a Lewis acid. These results are rationalized by calculation of stationary points on the potential energy surfaces for the various possible reaction pathways using ab initio molecular orbital methods. | en |
dc.language.iso | en | en |
dc.title | Directed Ring-Opening of 1,5-Dioxaspiro[3.2]hexanes: Selective Formation of 2,2-Disubstituted Oxetanes | en |
dc.type | Article | en |
local.publisher | Department of Chemistry, University of Nairobi | en |