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Positional selectivity during controlled oxidation of polyolefins

✍ Scribed by E.E. van Tamelen; K.B. Sharpless

Book ID
104241234
Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
253 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

In attempts to simulate the obligatory end double bond oxidation triggering the over-all biological conversion of squalene to sterols, van Tamelen and Curphey (1) observed several years ago the highly selective formation of terminal bromohydrin during attack of squalene by N-bromosuccinimide in aqueous ethylene glycol dimethyl ether. More recently, squalene-2, 3-oxide produced by this chemical means was shown in this (2) and another (3) laboratory to act as a biological precursor of lanosterol and cholesterol, suggesting that epoxidation at the A2 position of squalene initiates the biochemical sequence. Because of its intrinsic chemical novelty, its biological implications, and its actual utility in preparing artificial substrates for biochemical mechanistic studies. the non-enzymic selective terminal oxidation of terpenes and other olefins by means of various agents was investigated in more detail.

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