Carbenoid reactions of 2-halomethyl-4,6-dimethyl-s-triazines.
Reactions of lithium, sodium, and potassium salts of 2,4,6-trimethyl-s-triazine (1) with 2-halomethyl-4,6-dimethyl-s-triazine (2) (X = Cl, Br) in glyme have been studied and found to give 1,2-bis(4,6-dimethyl-s-triazin-2-yl)ethane (3), 1,2-bis(4,6-dimethyl-s-triazin-2-yl)ethene (5), 1,2,3-tris(4,6-dimethyl-s-triazin-2-yl)cyclopropane (6), 1,2,3-tris(4,6-dimethyl-s-triazin-2-yl)propane (7), and 1,2,3,4-tetrakis(4,6-dimethyl-s-triazin-2-yl)butane (8). It is proposed that product 3 is formed primarily via an S(N)2 reaction, whereas the remaining products are formed primarily via carbenoid reactions that are enumerated.
Stephens
Craig L
CL
Department of Chemistry, California State University, Northridge, California 91330-8262. USA.
Nyquist
H LeRoy
HL
Hardcastle
Kenneth I
KI
D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D017680:Potassium Compounds / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D017670:Sodium Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014227:Triazines / Q000737:chemistry*; D014961:X-Ray Diffraction
D006846:Hydrocarbons, Halogenated; D018020:Lithium Compounds; D017680:Potassium Compounds; D012492:Salts; D017670:Sodium Compounds; D014227:Triazines