Preparation of TlTpmenthyl

The products were redissolved in CH2Cl2 (300 cm3) and TlOAc (11.86 g, 0.045 mol) was added. The orange mixture was stirred at room temperature for 6 h. and then filtered. Removal of solvent from the filtrate under reduced pressure yielded a yellow solid that became white after washing with cold MeOH. The white solid was dried under vacuum (14.8 g, 56% yield):

1H NMR (CD2Cl2, 270M Hz) d 7.30 (s, 3H), 2.78 (m, 3H), 2.57 (m, 3H), 2.17 (br m, 3H), 1.94 (m, 3H), 1.74 (m, 6H), 1.41 (m, 3H), 1.14 (d, J = 6.96 Hz, 9H), 0.99 (d, J = 6.77 Hz, 9H), 0.84 (d, J = 6.78 Hz, 9H) ppm, 13C {1H} NMR (CD2Cl2, 67.5 MHz) d 152.5,132.9,121.1, 39.7, 32.2, 29.5, 27.3, 22.8, 21.9, 21.6, 18.7 ppm; IR (KBr) 2955, 2865, 2428 ([[nu]]B-H), 1553, 1451, 1384, 1307, 1144, 1012, 826, 775, 737, 715cm-1; MS (FAB+) (relative intensity) 954 (100), 748 (98), (FAB-) 542 (67), 169 (100). Anal. Calcd for C33H52N6BTl: C, 52.99; H, 7.01; N, 11.24. Found: C, 53.38; H, 7.20; N, 11.24.