Caglioti reduction

Reduction of tosylhydrazones (1, 1051 2, 377-378). The Caglioti reduction of tosylhydrazones has been extended to a synthesis of dimethyl alkanephos-phonates (2) from the tosylhydrazones (1). Reduction with sodium borohydride in THF results in formation of (2) reduction in methanol leads to dimethyl... 

Reduction of hydrazones (Wolff-Kishner and Caglioti reductions). 574... 

Reduction of tosylhydrazones. Caglioti (Univ. di Bologna, Italy) introduced a simple method for the deoxygenation of aliphatic aldehydes and ketones under mild and neutral conditions consisting in reaction of the tosylhydrazone with sodium borohydride in methanol.35,36... 

A very useful variant of the hydrazone reduction is the deoxygenation of aldehydes and ketones via the hydride reduction of tosylhydrazones (Caglioti reaction) The method is mild, convenient and widely applicable. While sodium borohydride was used in the earlier procedures, considerable improvements have been achieved through the uses of sodium cyanoborohydride, catecholborane, diborane, his-benzoyloxy borane and copper borohydride as reducing agents and HMPA, DMF, sulpholane, etc. as solvents. Use of the sterically crowded 2,4,6-triisopropyl tosylhydrazone derivative has greatly facilitated the reduction in some cases (equations 61-64). ... 

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