sncl2ticl3-mediated deoximation of oximes in an aqueous solventsncl2ticl3-mediated deoximation肟的水溶剂.pdfVIP

Molecules 2012, 17, 2464-2473; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article SnCl /TiCl -Mediated Deoximation of Oximes in an 2 3 Aqueous Solvent Mei-Huey Lin *, Han-Jun Liu, Cheng-Yu Chang, Wei-Cheng Lin and Tsung-Hsun Chuang Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan * Author to whom correspondence should be addressed; E-Mail: mhlin@.tw; Tel.: +886-4-723-2105 ext. 3543; Fax: +886-4-721-1190. Received: 30 January 2012; in revised form: 23 February 2012 / Accepted: 27 February 2012 / Published: 1 March 2012 Abstract: A simple procedure for SnCl /TiCl -mediated deoximation of ketoximes in an 2 3 aqueous solvent is reported. Under the conditions developed in this effort, various ketones and aldehydes are produced in good to excellent yields. Keywords: deoximation; aqueous solvent; ketoxime; aldoxime; tin chloride; titanium trichloride 1. Introduction Oximes are often used in organic synthesis as protected forms of carbonyl compounds [1] or as carbonyl derivatives for purification and characterization purposes [2]. Furthermore, oximes can be prepared from noncarbonyl compounds, such as nitroalkanes [3–5], or primary amines [6], thus deoximation provides an alternative approach for the syntheses of aldehydes and ketones. A plethora of examples of procedures for the regen