dc.contributor.author | Taboada, R | |
dc.contributor.author | Ordonio, GG | |
dc.contributor.author | Ndakala, AJ | |
dc.contributor.author | Howell, AR | |
dc.contributor.author | Rablen, PR | |
dc.date.accessioned | 2013-06-23T08:45:22Z | |
dc.date.available | 2013-06-23T08:45:22Z | |
dc.date.issued | 2003 | |
dc.identifier.citation | Taboada R, Ordonio GG, Ndakala AJ et al (2003). Directed ring-opening of 1,5-dioxaspiro[3.2]hexanes: selective formation of 2,2-disubstituted oxetanes. J Org Chem. 2003 Feb 21;68(4):1480-8. | en |
dc.identifier.uri | http://www.ncbi.nlm.nih.gov/pubmed/12585892 | |
dc.identifier.uri | http://erepository.uonbi.ac.ke:8080/xmlui/handle/123456789/38410 | |
dc.description.abstract | 1,5-Dioxaspiro[3.2]hexanes undergo ring-opening reactions with many heteroatom nucleophiles to provide alpha-substituted-beta'-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 pK(a) 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 |