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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2001

Autores

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

Revista

Título: Journal of Molecular Catalysis A: Chemical

Vol. 172

Páginas: 33-42

ISSN: 1381-1169

Editora: Elsevier B.V.

Indexação

ISI Web of Knowledge - 66 Citações

Scopus - 67 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 10