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tert-Butyl Hypoiodite

Simpkins, Nigel S. and Wirth, Thomas 2009. tert-Butyl Hypoiodite. In: Paquette, Leo A. ed. Encyclopedia of Reagents for Organic Synthesis (EROS). 2nd ed., Chichester: Wiley,

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Abstract

[917-97-5] C4H9IO (MW 200.02) InChI = 1S/C4H9IO/c1-4(2,3)6-5/h1-3H3 InChIKey = SFWFCZUSPDXUPN-UHFFFAOYSA-N (reagent for radical and ionic iodinations) Physical Data: orange–red solution, max 515 nm. Solubility: sol CCl4 and benzene. Form Supplied in: not commercially available. Preparative Methods: the reagent has not been isolated in pure form and its precise nature is uncertain. Reagents considered to be ‘tert-butyl hypoiodite’ have been commonly prepared by the reaction of t-Butyl Hypochlorite with either Iodine or metal iodide salts, or by the reaction of Potassium t-Butoxide with iodine. Tanner and co-workers have shown that the reagent generated by the first of these methods is quite different to that formed by the other two methods.1 Although the reagent formed by the latter two methods can be thought of as tert-BuOI, the actual structure of the reagent is uncertain and there may be slight differences in the composition of different batches. This situation is amply illustrated for the reaction of tert-BuOCl with AgI (eqs 1-4) The scheme adequately explains the spectroscopic and molecular weight measurements of the product formed in this way, and also the liberation of varying amounts of iodine (eq 4). (1) (2) (3) (4) Handling, Storage, and Precautions: reported to be very sensitive to moisture and is best generated in situ as required.

Item Type: Book Section
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: DOI for book 10.1002/047084289X.rb389.pub2
Publisher: Wiley
ISBN: 9780470017548
Related URLs:
Last Modified: 04 Jun 2017 03:47
URI: http://orca-mwe.cf.ac.uk/id/eprint/26579

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