N-iodosuccinimide mediated oxidative cleavage of vicinal, monoprotected diols

✍ Scribed by Chriss E. McDonald; Harald Holcomb; Todd Leathers; Francis Ampadu-Nyarko; James Frommer Jr.

• Book ID: 104228337
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 257 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97043-6

✦ Synopsis

Vbinal, monoprotected dials are cleaved to mixed acetals and carbonyl compounds upon treatment with N-bdosucclnimfde in the presence of light, base, and methanol. N-bdosucdnimide (NIS) has been shown to bs a versatile oxidant for the alcohol functtonaf groupP lnftially NIS converts the alcohol to a hypobdite. 3 The fate of ths hypoiodtle ts dependent on the presence