Efficient methods of synthesis of unsaturated alcohols and ketones by allylation of Favorsky reaction products under phase transfer conditions


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Abstract

Allylation of the Favorsky reaction products with allyl halides under phase-transfer catalysis in the system CuI–K2CO3–Na2SO3–BTEAC–H2O–C6H6 afforded the corresponding allylpropargyl alcohols in high yields (87–96%). The procedure is practical and scalable (more than 50 g of the target product can be prepared in a single run) and is characterized by high selectivity. Oxidation of secondary allylpropargyl alcohols with manganese dioxide in anhydrous acetonitrile at room temperature gave 75–81% of allylacetylenic ketones.

About the authors

V. A. Potapov

Favorsky Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

T. I. Yaroshenko

Favorsky Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

V. A. Panov

Favorsky Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

M. V. Musalov

Favorsky Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

A. G. Khabibulina

Favorsky Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

M. V. Musalova

Favorsky Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

S. V. Amosova

Favorsky Irkutsk Institute of Chemistry, Siberian Branch

Author for correspondence.
Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

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