10367-97-2Relevant articles and documents
Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis
Wang, Tao,Rabe, Patrick,Citron, Christian A.,Dickschat, Jeroen S.
, p. 2767 - 2777 (2013)
Two unidentified chlorinated volatiles X and Y were detected in headspace extracts of the fungus Geniculosporium. Their mass spectra pointed to the structures of a chlorodimethoxybenzene for X and a dichlorodimethoxybenzene for Y. The mass spectra of some constitutional isomers for X and Y were included in our databases and proved to be very similar, thus preventing a full structural assignment. For unambiguous structure elucidation all possible constitutional isomers for X and Y were obtained by synthesis or from commercial suppliers. Comparison of mass spectra and GC retention times rigorously established the structures of the two chlorinated volatiles. Chlorinated volatiles are not very widespread, but brominated or even iodinated volatiles are even more rare. Surprisingly, headspace extracts from Streptomyces chartreusis contained methyl 2-iodobenzoate, a new natural product that adds to the small family of iodinated natural products.
THE REACTIONS OF UNACTIVATED ARYL HALIDES WITH SODIUM METHOXIDE IN HMPA; SYNTHESIS OF PHENOLS, ANISOLES, AND METHOXYPHENOLS
Testaferri, L.,Tiecco, M.,Tingoli, M.,Chianelli, D.,Montanucci, M.
, p. 193 - 198 (1983)
Sodium methoxide reacts with dichlorobenzenes in HMPA to give the chloroanisoles as a result of a SNAr process.Excess MeONa then effects the demethylation of the ethers to give the chlorophenols via an SN2 reaction.With tri- and tetrachlorobenzenes the initially formed chloroanisoles can be dealkylated to chlorophenols or can suffer further substitution to give the chlorodimethoxybenzenes; these react with excess MeONa to give the chloromethoxyphenols.The results obtained with the various isomers of the di-, tri-, and tetrachlorobenzenes are presented and discussed on the basis of the electronic effects of the substituents.
