Oxidation of unsaturated monoterpenes with hydrogen peroxide catalysed by manganese(III) porphyrin complexes

• Type: Article in International Scientific Journal
• Date: 2001

Authors

Martins, RRL (Author) Other; Neves, MGPMS (Author) Other; Silvestre, AJD (Author) Other; Simoes, MMQ (Author) Other; Silva, AMS (Author) Other; Tome, AC (Author) Other; Cavaleiro, JAS (Author) Other; Tagliatesta, P (Author) Other; Crestini, C (Author) FCUP

Journal

Title: Journal of Molecular Catalysis A: Chemical

Vol. 172

Pages: 33-42

ISSN: 1381-1169

Publisher: Elsevier B.V.

Indexing

ISI Web of Knowledge - 66 Citations

Scopus - 67 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-000-TYN

DOI: 10.1016/s1381-1169(01)00120-0

Abstract (EN): Oxidation of (+)-3-carene (1), nerol (2) and geraniol (3) by hydrogen peroxide in the presence of catalytic amounts of several manganese(III) porphyrin complexes with electron withdrawing and electron donating groups was examined. The reactions were carried out at room temperature in acetonitrile, using aqueous hydrogen peroxide as oxidant and ammonium acetate as co-catalyst. The oxidation reactions of 3-carene (1) showed high conversion of the substrate with all metalloporphyrins tested and four major products were identified and characterised, namely alpha -3,4-epoxycarane (7), beta -3,4-epoxycarane (8), 3-caren-5-one (9) and 3-carene-2,5-dione (10). Nerol (2) oxidation reactions gave rise to 2,3-epoxynerol(ll), 6,7-epoxynerol (12) and 2,3,6,7-diepoxynerol (13). In the case of geraniol (3), besides 2,3-epoxygeraniol (14), 6,7-epoxygeraniol (15) and 2,3,6, 7-diepoxygeraniol (16), the oxidation reactions afforded 6,7-epoxygeranial (17). The terminal 6,7 double bond of nerol and geraniol was preferentially epoxidised. The regioselectivity induced by different porphyrins was investigated.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10