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Article << Previous     |     Next >>   Contents Vol 67(9)

Solvent-Free, Microwave-Assisted Conversion of Tosylates into Iodides*

Jia Cao A and Patrick Perlmutter A B

A School of Chemistry, Monash University, Wellington Road, Clayton, Vic. 3800, Australia.
B Corresponding author. Email: patrick.perlmutter@monash.edu

Australian Journal of Chemistry 67(9) 1360-1361 http://dx.doi.org/10.1071/CH14242
Submitted: 15 April 2014  Accepted: 19 May 2014   Published: 12 June 2014

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A highly efficient method for the conversion of primary tosylates into the corresponding iodides is outlined. The method involves heating a neat mixture of the tosylate and solid sodium iodide in a microwave cavity. Reaction times are short, usually about 60 minutes, delivering high yields. This procedure is especially useful for the in situ generation of volatile primary iodides, and for most of the primary iodides, the crude product is sufficiently pure.


[1]  C. Jia, P. Perlmutter, Org. Lett. 2013, 15, 4237.

[2]  N. M. O’Connell, Y. C. O’Callaghan, N. M. O’Brien, A. R. Maguire, F. O. McCarthy, Tetrahedron 2012, 68, 4995.
         | CrossRef | CAS |

[3]  H. Finkelstein, Ber. Dtsch. Chem. Ges. 1910, 43, 1528.
         | CrossRef | CAS |

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