Iodobenzene catalyzed iodolactonisation using sodium perborate monohydrate as the end oxidant

ORGN 165

Hongjun Liu, g0600468@nus.edu.sg and Choon-Hong Tan, chmtanch@nus.edu.sg. Department of Chemistry, National University of Singapore, 3 Science Drive 3,S8-03-01,117543, Singapore, Singapore
A convenient approach has been developed for iodolactonisation using iodobenzene as catalyst. The active reagent was identified as diacetyloxyiodate(I) and was generated in situ with tetra-n-butylammonium iodide (TBAI) and hypervalent iodine reagent, diacetoxyiodobenzene (PIDA). PIDA, in turn, was generated in situ using a catalytic amount of iodobenzene with sodium perborate monohydrate as the stoichiometric oxidant. A variety of olefinic acids including ä-pentenoic acids, ä-pentynoic acids and ä-hexynoic acid gave high yields of lactones using this methodology.
 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008