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Review
. 2006 Jun 20;11(6):421-34.
doi: 10.3390/11060421.

Hypervalent iodine-mediated ring contraction reactions

Luiz F Silva Jr  1
Affiliations
Review

Hypervalent iodine-mediated ring contraction reactions

Luiz F Silva Jr. Molecules. .

Abstract

Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)- iodo]benzene (Koser' s reagent). This review covers all the literature related to the ring contraction of cyclic ketones and olefins promoted by iodine(III) species.

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Figures

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Figure 1
Structure of the Intermediates proposed by Daum.
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Reagents and Conditions: 0.92 eq. PhI(OH)Ts; 95% MeOH, rt. Reaction times: 54: 20 min; 55: 1 h and; 56: 8h.
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Scheme 21
See this image and copyright information in PMC

References

    1. Silva L. F., Jr. Tetrahedron. 2002;58:9137–9161. doi: 10.1016/S0040-4020(02)00990-0. - DOI
    1. Ferraz H. M. C., Silva L. F., Jr. Quim. Nova. 2000;23:216–224.
    1. Ferraz H. M. C., Aguilar A. M., Silva L. F., Jr. Tetrahedron. 2003;59:5817. doi: 10.1016/S0040-4020(03)00974-8. - DOI
    1. Wirth T. Oxidations and rearrangements. In: Wirth T., editor. Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis. Springer-Verlag; Weinheim: 2003. pp. 185–208.
    1. Dauban P., Dodd R. H. Synlett. 2003:1571–1586. doi: 10.1055/s-2003-41010. - DOI

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