Solvent Free, Microwave Assisted Conversion of Aldehydes into Nitriles and Oximes in the Presence of NH2OH·HCl and TiO2 英文参考文献.docVIP

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Solvent Free, Microwave Assisted Conversion of Aldehydes into Nitriles and Oximes in the Presence of NH2OH·HCl and TiO2 英文参考文献.doc

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Solvent Free, Microwave Assisted Conversion of Aldehydes into Nitriles and Oximes in the Presence of NH2OH·HCl and TiO2 英文参考文献

Molecules 2010, 15, 94-99; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Solvent Free, Microwave Assisted Conversion of Aldehydes into Nitriles and Oximes in the Presence of NH2OH·HCl and TiO2 Lucas Villas-Boas Hoelz, Biank Tomaz Gon?alves, José Celestino Barros and Joaquim Fernando Mendes da Silva * Departamento de Química Organica, Instituto de Química, Universidade Federal do Rio de Janeiro, Av. Athos da Silveira Ramos 149, CT Bloco A, Cidade Universitária, Rio de Janeiro, RJ 21941-909, RJ, Brazil * Author to whom correspondence should be addressed; E-Mail: joaquim@iq.ufrj.br. Received: 27 October 2009; in revised form: 22 December 2009 / Accepted: 23 December 2009 / Published: 29 December 2009 Abstract: Aromatic aldehydes bearing electron-donating groups are easily converted into their respective nitriles using NH2OH·HCl and TiO2 under microwave irradiation, while those bearing an electron-withdrawing group give the corresponding oximes. Keywords: titanium dioxide; aldehydes; nitriles; oximes; microwave irradiation 1. Introduction Titanium dioxide (TiO2) has attracted the attention of synthetic organic chemists due to its application as a heterogeneous catalyst and as a photocatalyst. In addition, TiO2 is inexpensive, non- toxic and safe [1]. TiO2 may complex with the carbonyl oxygen atoms of aldehydes and ketones, thus activating them for nucleophilic attack [2]. Sharghi and Sarvari converted aldehydes and ketones into the respective amides in the presence of NH2OH·HCl and TiO2 in a one-pot, solvent free procedure, but with long reaction times [3]. Aldehydes may also be converted into their respective nitriles in good yields and short reaction times using NH2OH·HCl under microwave irradiation using, however, the toxic N-methyl-2-pyrrolidinone (NMP) as solvent [4]. In the two cases, the mechanism involves oxime generation, but while the amides are o