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Halo- and selenolactonisation: The two major strategies for cyclofunctionalisation
Published in Elsevier Ltd
2004
Volume: 60
   
Issue: 25
Pages: 5273 - 5308
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.

About the journal
JournalData powered by TypesetTetrahedron
PublisherData powered by TypesetElsevier Ltd
ISSN00404020
Open AccessNo
Authors (3)