Halo- and selenolactonisation: the two major strategies for cyclofunctionalisation

Ranganathan, S and Muraleedharan, KM and Vaish, NK and Jayaraman, N (2004) Halo- and selenolactonisation: the two major strategies for cyclofunctionalisation. In: Tetrahedron, 60 (25). pp. 5273-5308.

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Abstract

At the turn of the 20th century, Bougoult made a detailed and systematic study of the conversion of b,g- and g,d-unsaturated carboxylic acids to iodolactones with iodine in aqueous NaHCO3. He showed that, when the double bond was further removed from the carboxylic acid functionality, no reaction took place. He considered that these reactions involved the addition of nascent hypoiodous acid, followed by lactonisation of the resulting hydroxy acid.1 Intervening developments in this area as well as in mechanistic studies enabled van Tamelen and Shamma to propose, in 1954, the currently accepted view of this process, namely that halolactonisation arise by the intramolecular carboxylic acid-mediated opening of the initially-formed halonium ion intermediate.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier
Additional Information:	Copyright of this article belongs to Elsevier.
Keywords:	carboxylic acid;lactonisation;stereoselectivity.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	19 Dec 2008 04:46
Last Modified:	19 Sep 2010 04:55
URI:	http://eprints.iisc.ac.in/id/eprint/17032

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