Abstract
Photolysis of a nitrite ester to a γ-oximino alcohol.
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References
(a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640–2641. In 1960, Derek Barton took a “vacation” in Cambridge, Massachusetts; he worked in a small research institute called the Research Institute for Medicine and Chemistry. In order to make the adrenocortical hormone aldosterol, Barton invented the Barton nitrite photolysis by simply writing down on a piece of paper what he thought would be an ideal process. His skilled collaborator, Dr. John Beaton, was able to reduce it to practice. They were able to make 40 to 50 g of aldosterol at a time when the total world supply was only about 10 mg. Barton considered it his most satisfying piece of work. (b) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1960, 82, 2641–2641. (c) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083–4089. (d) Barton, D. H. R.; Lier, E. F.; McGhie, J. M. J. Chem. Soc., (C) 1968, 1031–1040.
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Li, J.J. (2014). Barton nitrite photolysis. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_15
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