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Burgess reagent is a selective dehydrating reagent used in organic synthesis. It is used to convert secondary and tertiary alcohol, with an adjacent proton, into alkenes. Burgess reagent is also utilized to promote great synthetic values in medicinal chemistry. It has been used in dehydration of primary amides, formamides and primary nitroalkanes to generate nitriles, isocyanides and nitrile oxides respectively. It forms urethanes when it reacts with primary alcohols.
Mild, efficient dehydrating agent. Primary alcohols are converted to carbamates, which can be hydrolyzed to primary amines, thus providing a valuable alcohol to amine transformation. Secondary and tertiary alcohols afford olefins in synthetically useful yields: J. Org. Chem., 38, 26 (1973); Org. Synth. Coll., 6, 788 (1988). For further discussion, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 5, p. 3345.
Primary amides undergo facile dehydration to nitriles, even in the presence of other functional groups including alcohols: Tetrahedron Lett., 29, 2155 (1988). Aldoximes are also dehydrated to nitriles: Synth. Commun., 30, 1509 (2000); Synlett, 1169 (2000). Formamides afford isonitriles: J. Chem. Soc., Perkin 1, 1015 (1998). 2-Acylamino carbonyl compounds undergo the Robinson-Gabriel cyclodehydration to give oxazoles, avoiding conventional harsh dehydrating agents (e.g. P2 O5, POCl3 or SOCl2 ): Synlett, 1642 (1999):
The cyclization of 1,2-diacylhydrazines to 1,3,4-oxadiazoles has also been reported: Tetrahedron Lett., 40, 3275 (1999).
Majid, M. H.; Tahereh, A.; Azadeh, F.; Nasim, M. K. Recent Advances in the Application of the Burgess Reagent in Organic Synthesis. Curr. Org. Synth. 2015, 12 (3), 328-357.
Maki, T.; Tsuritani, T.; Yasukata, T. A Mild Method for the Synthesis of Carbamate-Protected Guanidines Using the Burgess Reagent. Org. Lett. 2014, 16 (7), 1868-1871.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P501c
Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant