Synthesis of New Cardanol and Cardol Derivatives by Allylation and Regioselective­ Cyclocarbonylation Reactions

Riccardo Amorati; Orazio A. Attanasi; Bassam El Ali; Paolino Filippone; Giuseppe Mele; Jolanda Spadavecchia; Giuseppe Vasapollo

doi:10.1055/s-2002-35983

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Synthesis of New Cardanol and Cardol Derivatives by Allylation and Regioselective Cyclocarbonylation Reactions

Riccardo Amorati^a, Orazio A. Attanasi^b, Bassam El Ali^d, Paolino Filippone*^b, Giuseppe Mele^c, Jolanda Spadavecchia^c, Giuseppe Vasapollo*^c
^a Dipartimento di Chimica Organica ‘A. Mangini’, Università di Bologna, Via S. Donato 15, 40127 Bologna, Italy
^b Centro di Studio delle Sostanze Organiche di Origine Naturale, Università di Urbino, Piazza della Repubblica 13, 61029 Urbino, Italy
^c Dipartimento di Ingegneria dell’Innovazione, Università di Lecce, Via Arnesano, 73100 Lecce, Italy
^d Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahram 31261, Saudi Arabia
e-Mail: attor@uniurb.it;

Abstract

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Abstract

Palladium acetate [Pd(OAc)₂] and 1,4-bis(diphenylphosphino)butane (dppb) catalyse cyclocarbonylation of allylic cardanol and cardol derivatives to give regioselectively 7-membered ring lactones in good yields. One of the compounds prepared exhibits excellent antioxidant properties.

Key words

allylations - carbonylations - cardanol - cardol - lactones - palladium

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Synthesis of New Cardanol and Cardol Derivatives by Allylation and Regioselective­ Cyclocarbonylation Reactions

Synthesis of New Cardanol and Cardol Derivatives by Allylation and Regioselective Cyclocarbonylation Reactions