Corrigendum to “Solvent-free synthesis of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one from Dess–Martin periodinane and its synthetic utility for α-tosyloxylation of ketones”: [Tetrahedron Lett. 49 (2008) 3441]

✍ Scribed by Nandkishor N. Karade; Girdharilal B. Tiwari; Sandeep V. Shinde; Sumeet V. Gampawar; Jeevan M. Kondre

• Book ID: 104095660
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 115 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.07.118

✦ Synopsis

The authors regret that the reaction of Dess-Martin periodinane with p-toluenesulfonic acid monohydrate using a grinding technique does not lead to the formation of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 8 as reported in the above Letter. 1-(p-Toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 8 is not formed for the following reasons:

1. The melting point of the compound resulting from grinding of Dess-Martin periodinane with p-toluenesulfonic acid monohydrate is 130-132 °C, which is different from the literature value (178-180 °C). 1 2. There is no suitable mechanistic explanation for the formation of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 8 from the reaction of Dess-Martin periodinane with p-toluenesulfonic acid monohydrate using a grinding technique.

In conclusion, the reaction of Dess-Martin periodinane with p-toluenesulfonic acid monohydrate under grinding conditions does not lead to the formation of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 8. However, this mixture can induce a-tosyloxylation of enolizable ketones.