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4
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0041908469
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Kumara Swamy K.C., Kumaraswamy S., Said M.A., Krishna Kishore R.S., Herbst-Irmer R., and Pülm M. Curr. Sci. 78 (2000) 473
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Curr. Sci.
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, pp. 473
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Kumara Swamy, K.C.1
Kumaraswamy, S.2
Said, M.A.3
Krishna Kishore, R.S.4
Herbst-Irmer, R.5
Pülm, M.6
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7
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0001378116
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Lacour J., Londez A., Goujon-Ginglinger C., Buss V., and Bernardinelli G. Org. Lett. 2 (2000) 4185
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(2000)
Org. Lett.
, vol.2
, pp. 4185
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Lacour, J.1
Londez, A.2
Goujon-Ginglinger, C.3
Buss, V.4
Bernardinelli, G.5
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9
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0037450928
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Hebbe V., Londez A., Goujon-Ginglinger C., Meyer F., Uziel J., Jugé S., and Lacour J. Tetrahedron Lett. 44 (2003) 2467
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(2003)
Tetrahedron Lett.
, vol.44
, pp. 2467
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Hebbe, V.1
Londez, A.2
Goujon-Ginglinger, C.3
Meyer, F.4
Uziel, J.5
Jugé, S.6
Lacour, J.7
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16
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0842328434
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Kommana P., Satish Kumar N., Vittal J.J., Jayasree E.G., Jemmis E.D., and Kumara Swamy K.C. Org. Lett. 6 (2004) 145
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(2004)
Org. Lett.
, vol.6
, pp. 145
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Kommana, P.1
Satish Kumar, N.2
Vittal, J.J.3
Jayasree, E.G.4
Jemmis, E.D.5
Kumara Swamy, K.C.6
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17
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1642282138
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Satish Kumar N., Praveen Kumar K., Pavan Kumar K.V.P., Kommana P., Vittal J.J., and Kumara Swamy K.C. J. Org. Chem. 69 (2004) 1880
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(2004)
J. Org. Chem.
, vol.69
, pp. 1880
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Satish Kumar, N.1
Praveen Kumar, K.2
Pavan Kumar, K.V.P.3
Kommana, P.4
Vittal, J.J.5
Kumara Swamy, K.C.6
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19
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67349285291
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31P NMR: δ 168.3 {lit 168.4 [5c]}.
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31P NMR: δ 168.3 {lit 168.4 [5c]}.
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20
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67349234019
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S{6-t-Bu-4-Me-C6H2O}2]2P+Cl, C3H4N2, 8, and the solid 7, To a stirred solution of 5 (0.92 g, 2.2 mmol) in toluene (20 mL) at -78 °C was added DIAD (0.45 g, 2.2 mmol) through a syringe over a period of 5 min. The reaction mixture was brought to room temperature and stirred for 12 h; then the solvent was evaporated and the residue crystallized from heptane-dichloromethane (2, 0.5 mL) mixture. This reaction mixture showed δ (31P) 71.0, 90.3 (br) corresponding to 6. When the reaction was performed in the presence of pyrazole (2.2 mmol) using the in situ generated 6, compound 8 separated out, followed by 7 (ca 0.5 g, Yield (8, 0.2 g (ca 10, 1H NMR: δ 1.02 and 1.53 (2 s, 36 H, Ar-C(CH3)3, 2.36 (s, 12 H, ArCH3, 4.83 (m, 2 H, OCH(CH3)2, 6.38 (br s, 1 H, pyrazolyl-H) 7.23-7.64 m, 5 H, Ar-H
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2: C 65.53; H, 6.99; N, 6.11, S 6.99. Found: C, 65.42; H, 7.04; N, 6.04; S, 6.88. Although this compound could be detected in another reaction containing additional diol, isolation of a pure material could not be accomplished in that case.
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24
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67349169682
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note
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31P NMR spectrum [δ(P): -3.4, -13.7, -18.4 with the last one predominating when a higher stoichiometry of pyrazole was used] of the resulting mixture showed peaks only in the tetracoordinate region.
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25
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67349208352
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X{6-t-Bu-4-Me-C6H2O}2]POCH2CH2SH [X, S (10, CH2 (11, Compound [CH2{6-t-Bu-4-Me-C6H2O}2]PCl (9) was prepared by a method reported by us before [6a, Compounds 10 and 11 were prepared in ≥80% yield by treating 5 or 9 with 2-mercapto ethanol in the presence of Et3N in toluene. Compound 10: Semisolid. 1H NMR (400 MHz, CDCl3) δ 1.42 (s, 18H, 2CH(CH3)3, 2.28 (s, 6H, ArCH3, 2.89-2.91 (m, 2H, SCH2, 4.26-4.28 (m, 2H, OCH2, 7.12-7.34 (4H, Ar-H, 13C NMR (100 MHz, CDCl3) δ 20.8, 26.2 (d, J, 5.7 Hz, 30.0, 35.2, 65.9 (d, J, 27.4 Hz, 123.0 (d, J, 2.8 Hz, 128.3, 129.1 (d, J, 26.0 Hz) 133.5, 140.6, 153.4 (d, J, 7.5 Hz, 31P NMR (160 MHz, CDCl3) δ, 142.7; LC/MS m/z 464 [M+1, Compound 11: mp 160-164 °C; 1
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+.
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26
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67349214556
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Compound 12: To a stirred solution of 10 (0.69 g, 2.80 mmol) in dry toluene (10 mL, was added o-chloranil (1.30 g, 2.80 mmol) at room temperature and the reaction was continued until the color of o-chloranil disappeared (12 h, Removal of solvent in vacuo to gave 12 as a gummy solid. Yield 1.39 g (70, 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 18H, 2 CH(CH3)3, 2.26 (s, 6H, 2 PhCH3, 2.79-2.84 (m, 2H, SCH2, 2.95-2.96 (m, 1H, CHACHB, 4.28-4.30 (m, 2H, OCH2, 4.40-4.42 (m, 1H, CHACHB, 7.00-7.41 (4H, ArH, 13C NMR (100 MHz, CDCl3) δ 20.8, 21.5, 25.3, 25.4, 29.4, 35.0, 39.1, 46.0, 65.6, 68.7 (d, J, 8.0 Hz, 114.8 (d, J, 20.0 Hz, 119.2 (d, J, 9.0 Hz, 124.2, 125.3, 128.2, 129.0, 129.8, 131.0, 131.6 (d, J, 6 .0 Hz, 137.9 (d, J, 8.0 Hz, 140.4 (d, J, 6.0 Hz, 151.4 (d, J, 9.0 Hz, 31P NMR (160 MHz, CDCl3) δ
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+.
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27
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67349106613
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Compound 13: To a stirred solution of 162 (0.20 g, 0.45 mmol) in dry toluene (10 mL, was added DIAD (0.09, 0.45 mmol) through syringe slowly at room temperature and the reaction was continued until the color of DIAD disappeared (12 h, The solvent was removed in vacuo to obtain 13. Yield 0.61 g (75, mp 160-164 °C; 1H NMR (400 MHz, CDCl3) δ 1.27 (d, J, 6.0 Hz, CH(CH3)2, 1.32 for major isomer (s, 18H, 6C(CH3)3, 1.41 for minor (s, 18H, 6C(CH3)3, 2.28 for major isomer (s, 6H, PhCH3, 2.36 for minor isomer 2.89-2.91 (s, 6H, PhCH3) 2.91 (m, 2H, SCH2, 3.44-3.47 (m, 1H, CHACHB, 4.34-4.39 (m, 1H, CHACHB, 4.45-4.47 (m, 2H, OCH2, 4.95-5.03 (m, 1H, CH(CH3)2, 6.98-7.27 (m, 4H, Ar-H, 13C NMR (100 MHz, CDCl3) δ 20.9, 21.5, 21.7, 22.0, 30.7, 34.8, 70.0, 125
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+.
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28
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67349192064
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note
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4P: C, 59.43; H, 6.10; N, 1.94. Found: C, 59.65; H, 6.14; N, 1.98.
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31
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67349145864
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note
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-3.
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34
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67349162003
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G.M. Sheldrick, SHELXTL NT Crystal Structure Analysis Package, Bruker AXS, Analytical X-ray System, WI, USA, 1999, version 5.10
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G.M. Sheldrick, SHELXTL NT Crystal Structure Analysis Package, Bruker AXS, Analytical X-ray System, WI, USA, 1999, version 5.10.
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35
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67349084559
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note
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We had assigned a different geometry 14′ for this compound before Ref. [6b].{A figure is presented}
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