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1,3-Dimethoxybenzene is used for the preparation of oxathiane spiroketal donors. It is also used for the formation of pi- and O-ylidic complexes with dichlorocarbene. Further, it acts as a flavoring agent.
Is readily metallated at the 2-position by n-BuLi, giving a lithio-derivative which is doubly-stabilized by oxygen coordination. For reviews, see: Org. React., 8, 258 (1954); 26, 1 (1979). The 2-lithio-derivative undergoes silylation, and the resulting silyl derivative reacts with electrophiles to give various 2-substituted products. For examples, see: Tetrahedron, 49, 10843 (1993):
Although direct dilithiation with n-BuLi/TMEDA was unsuccessful, a sequence involving monolithiation, silylation and further lithiation at the 4-position gave the 2,4-disilyl derivative in 47% yield: J. Org. Chem., 49, 4657 (1984). For a review of the use of organosilicon intermediates in unusual electrophilic substitutions, see: Synlett, 171 (1993).
Wang, Q.; Qi, Z.; Xie, F.; Li, X. Lewis Acid-Catalyzed Electrophilic Trifluoromethylthiolation of (Hetero)Arenes. Adv. Synth. Catal. 2015, 357 (2-3), 355-360.
Tran, P. H.; Hansen, P. E.; Nguyen, H. T.; Le, T. N. Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation. Tetrahedron Lett. 2015, 56 (4), 612-618.
Hazard Statements: H227
Precautionary Statements: P261-P280h
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