The 2-bromomethyl-3,5,6,7-tetrahydrobenzofuran-4-ones 1 were subjected to tetrachlorosilane and sodium azide (SiCl₄-NaN₃) in acetonitrile to afford tetrahydrotetrazolofuroazepine derivatives. Under similar reaction conditions, the 2-iodomethyl-3,5,6,7-tetrahydrobenzofuran-4-ones affords mixtures of products characterized as tetrahydrotetrazolofuroazepines 2 (major) and the 4-azido-2-iodomethyl-2,3-dihydrobenzofuran derivatives 3. We have recently described the synthesis and further studies of chemical transformation of 2-bromomethyl- and 2-iodomethyl-3,5,6,7- tetrahydrobenzofuran-4-ones 1 [1].

The results and the mechanism of formation of tetrahydrotetrazolofuroazepines 2 (major) and the 4-azido-2-iodomethyl-2,3-dihydrobenzofuranderivatives 3 is proposed [2].

[1] M. J. Mphahlele, T. B. Moekwa, Org. Biomol. Chem. 2005, 3, 2469.

[2] M. J. Mphahlele, T. B. Moekwa, J. Heterocyclic Chem., accepted.

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1. Regio- versus Non-Regioselectivity of Haloenolcyclization of 2-Allylcyclo-1,3-hexanediones Using Iodine in Methanol and Pyridinium tribromide in Dichloromethane