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Note | Regular issue | Vol 65, No. 6, 2005, pp.1425-1430
Published online, 15th April, 2005
DOI: 10.3987/COM-05-10357
Reactions of Bis(silyl-substituted) Methyllithium with α-Hydrogen-free Nitriles into 1,3,5-Triazines

Xia Chen, Sheng-Di Bai, Li Wang, and Dian-Sheng Liu*

*School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China


Bis(silyl-substituted) methyllithium has been found to catalyze a conversion of α-hydrogen-free nitriles directly to yield 2,4,6-trisubsituted s-triazines. The generally high yields and relatively mild reaction conditions of this procedure suggest an alternative to other aromatic nitrile cyclotrimerization reactions. Silicotropic rearrangements from C to N or N to N and an unusual elimination of LiCR2R’ (R=SiMe3, R’=SiMe2NMe2) were observed.