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With tetrakis(dimethylamido)diborane; In toluene; at 20 - 100℃; for 1.25h;
HEXYLENEGLYCOL (2-methyl-2,4-pentanediol) (FW: 118. 18. 12.0 g, 101. 6 mmol) in toluene (40 mL) was treated with tetrakis (dimethylamino) diboron (FW: 197.926 ; 9.9 g, 50 mmol) at room temperature and the reaction mixture stirred. The temperature was raised to 100 C within 10 minutes while the release of dimethylamine started to occur after about 5 minutes. The temperature was maintained at 100 C. for 60 minutes at which time for 30 minutes the evolution of dimethylamine occurred. Toluene was removed to give a solid (99.6percent pure by GC). The solid was recrystallised from toluene: petroleum (80 C-100 C) (1: 9) to give a colourless solid of bis (hexylene glycolato) diboron (MF: C12H24B204 ; FW : 253.94) : 8. 83 g, second crop: 3.69 g, combined yield 12.52 g, 98. 6percent; 99.6percent pure by GC. mp 99-101. 6 C. 8 (CDC13, 200 MHz) 1.21 (d, J= 7Hz, 6H); 1.28 (s, 12H); 1.47 (dd, J=12,14 Hz, 2H); 1.70 (dd, J=14,3 Hz; 2H) 4.14 (dm, 2H) ppm. 13C 8 (CDCL3, 50 MHz) 23.1 ; 28.3 ; 31.2 ; 46. 2 ; 64.1 ; 70.3 ppm.
Example 16 4,4,4',4',6,6'-Hexamethyl-2,2'-bi-1,3,2-dioxaborinane This diboronic ester is prepared following general procedure A using 2-methyl-2,4-pentanediol. Yield, 71percent. 1H-nmr (CDCl3, 200 MHz): delta 1.18-1.32 (multiplet, 18H; 6*CH3), 1.44-1.56 (multiplet, 2H; 2*HCHC), 1.69-1.78 (multiplet, 2H; 2*HCHC) and 4.07-4.22 (multiplet, 2H; 2*OCH). F.W.: calc. for C12H24B2O4=253.94, found m/z 255 (M+1).
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