Tetrahedron Letters

First green protocols for the large-scale preparation of γ-diisoeugenol and related dihydro (1H) indenes via formal [3+ 2] cycloaddition reactions

VV Kouznetsov, DRM Arenas

Index: Kouznetsov, Vladimir V.; Merchan Arenas, Diego R. Tetrahedron Letters, 2009 , vol. 50, # 14 p. 1546 - 1549

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Citation Number: 17

Abstract

Trans-isoeugenol and related styrenes (trans-isohomogenol or O-benzylated isoeugenol), important components of the essential oil of various tropical plants, dimerize easily in the presence of catalytic amounts of BF3· OEt2 in poly (ethylene glycol) with Mn= 400 (PEG- 400) or SiO2–OSO3H in MeCN via formal [3+ 2] cycloaddition reaction to give respective natural products (diisoeugenol and its O-substituted analog) with the 1, 2-trans-2, 3-trans- ...