S. K. Maiti, S. Dinda, S. Banerjee, A. K. Mukherjee, R. Bhattacharyya
FULL PAPER
[9]
a) H. Mimoun, I. Seree de Roch, L. Sajus, Bull. Soc. Chim. Fr.
1969, 5, 1481–1492; b) H. Mimoun, The Chemistry of Peroxide
(Ed.: S. Patai), John Wiley and Sons, New York, 1998, ch. 15;
c) W. R. Thiel, J. Eppinger, Chem. Eur. J. 1997, 3, 696–705; d)
W. R. Thiel, M. Angstl, N. Hansen, J. Mol. Catal. A 1995, 103,
5–10.
a) X. Zuwei, Z. Ning, S. Yu, L. Kunlan, Science 2001, 292,
1139–1141; b) K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, R.
Noyori, J. Org. Chem. 1996, 61, 8310–8311.
a) A. Berkessel, C. A. Sklorz, Tetrahedron Lett. 1999, 40, 7965–
7968; b) D. de Vos, T. Bein, Chem. Commun. 1996, 917–918; c)
B. S. Lane, K. Burgess, Chem. Rev. 2003, 103, 2457–2473; d)
E. M. McGarrigle, D. G. Gilheany, Chem. Rev. 2005, 105,
1563–1602.
M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc.
2001, 123, 7194–7195.
a) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J.
Am. Chem. Soc. 1997, 119, 6189–6190; b) W. A. Hermann,
R. W. Fischer, D. W. Marz, Angew. Chem. 1991, 103, 1706–
1709; Angew. Chem. Int. Ed. Engl. 1991, 30, 1638–1641; c) S.
Dinda, S. Roy Chowdhury, K. M. Abdul Mailk, R. Bhattach-
aryya, Tetrahedron Lett. 2005, 46, 339–341.
G. B. Payne, P. H. Willams, J. Org. Chem. 1959, 24, 54–55.
a) C. Venturello, R. D’Aloisio, J. C. Bart, M. Ricci, J. Mol.
Catal. 1985, 32, 107–110; b) C. Venturello, E. Alneri, M. Ricci,
J. Org. Chem. 1983, 48, 3831–3833.
T. Oguchi, Y. Sakata, N. Takeuchi, K. Kaneda, Y. Ishii, M.
Ogawa, Chem. Lett. 1989, 18, 2053–2056.
a) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977–
1986; b) ref.[11]; c) K. Sato, M. Aoki, M. Ogawa, T. Hashimoto,
D. Pasyella, R. Noyori, Bull. Chem. Soc. Jpn. 1997, 70, 905–
915.
S. K. Maiti, S. Banerjee, A. K. Mukherjee, K. M. Abdul Malik,
R. Bhattacharyya, New J. Chem. 2005, 29, 554–563.
S. K. Maiti, S. Dinda, N. Gharah, R. Bhattacharyya, New J.
Chem. 2006, 30, 479–489.
a) N. Gharah, S. Chakraborty, A. K. Mukherjee, R. Bhattach-
aryya, Chem. Commun. 2004, 2630–2632; b) S. K. Maiti,
K. M. A. Malik, S. Gupta, S. Chakraborty, A. K. Ganguly,
A. K. Mukherjee, R. Bhattacharyya, Inorg. Chem. 2006, 45,
9843–9857.
a) T. Yamada, T. Mukaiyama, Chem. Lett. 1989, 519–522; b)
A. J. Bailey, W. P. Griffith, S. I. Mostafa, P. A. Sherwood, In-
org. Chem. 1993, 32, 268–271; c) C. Zondervan, R. Hage, B. L.
Feringa, Chem. Commun. 1997, 419–420; d) R. A. Sheldon,
I. W. C. E. Arends, G. J. T. Brink, A. Djiksman, Acc. Chem.
Res. 2002, 35, 774–781; e) I. E. Marko, P. R. Giles, M. Tsuka-
zaki, I. Chelle-Regnaut, A. Gautier, R. Dumeunier, F. Phil-
ippart, K. Doda, J. L. Mutonkole, S. M. Brown, C. J. Urch,
Adv. Inorg. Chem. 2004, 56, 211–240.
a) P. Huston, J. H. Espenson, A. Bakac, Inorg. Chem. 1993, 32,
4517–4523; b) W. Adam, C. M. Mitchell, C. R. Saha-Moller,
Tetrahedron 1994, 50, 13121–13124; c) M. Bonchio, G. Licini,
F. Di Furia, S. Mantovani, G. Modena, W. A. Nugent, J. Org.
Chem. 1999, 64, 1326–1330; d) T. S. Smith II, V. L. Pecoraro,
Inorg. Chem. 2002, 41, 6754–6760; e) J. Legros, C. Bolm, An-
gew. Chem. Int. Ed. 2004, 43, 4225–4228.
Procedure III: Sulfones were crystallized out as solids after concen-
trating the aqueous layer, while unreacted sulfides and sulfoxides
remaining in the CH2Cl2 layer were separated by fractional distil-
lation. 1,4-benzoquinone (from phenol) was extracted out from the
reaction solution by diethyl ether and evaporation of ether deposits
on the off-white material. The mixture of products, 1,4-benzoqui-
none and 4-nitroaniline, obtained from 1,4-diaminobenzene was
separated by steam distillation, since the former is steam volatile.
Other amines and their oxidized products were separated by col-
umn chromatography, and their identities were checked by NMR
spectroscopic analysis. It may be mentioned that for all the above
procedures the amount of products chemically separated corre-
spond closely to the G.C. results.
[10]
[11]
[12]
[13]
Recovery of Catalyst: The residue left after distilling the ether and
acetonitrile off at mildly reduced pressure was thoroughly shaken
with diethyl ether repeatedly to extract the substrates and products
almost quantitatively from the ether solvent, and the yellow solid
residue left was verified by IR spectroscopy to be the catalyst.
Supporting Information (see footnote on the first page of this arti-
cle): The detailed chemical reactions for Scheme 3 and Scheme 4 as
mentioned in the text, the list of IR and UV/Vis spectral values,
the bond lengths and angles for all complexes, the method of deter-
mination of GC yield and the 183W NMR and mass spectra.
[14]
[15]
[16]
[17]
CCDC-662003, CCDC-662004, CCDC-662005 and CCDC-662006
for the structures of complexes 1, 2, 3 and 5, respectively, contain
the supplementary crystallographic data for this paper. These data
can be obtained free of charge from The Cambridge Crystallo-
graphic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
[18]
[19]
[20]
Acknowledgments
The authors thank the University Grants Commission (UGC) De-
partment of Special Assistance (DSA) and Council of Scientific
and Industrial Research (CSIR), New Delhi for financial assist-
ance. The authors also thank Department of Science and Technol-
ogy (DST), Government of India, for providing the funding for the
Agilent 6890N gas chromatograph. The authors also thank Prof.
P. Mathur (IIT, Bombay) for providing with the X-ray crystallo-
graphic data for one of the complexes and Dr. S. Ragothama (IISc,
Bangalore) for recording the 183W NMR spectroscopic data.
[21]
[1] P. Davis, R. T. Donald, N. H. Harvard, Catalyst Handbook
(Ed.: M. V. Twig), 2nd ed., Manson Publishing Ltd., London,
1996.
[22]
[23]
[2] a) R. C. Bray, The Enzymes (Ed.: P. D. Boyed), 3rd ed., Aca-
demic Press, New York, 1975, vol. 12, part B., ch. 6; b) M. P
Coughton (Ed.), Molybdenum and Molybdenum-Containing En-
zymes, Pergamon, New York, 1980; c) W. E. Newton, S. Ot-
seeka (Eds.), Molybdenum Chemistry of Biological Significance,
Plenum, Newyork, 1980; d) S. P. Cramer, R. Wahl, K. V. Rajag-
opalan, J. Am. Chem. Soc. 1981, 103, 7721–7727.
[3] Z. Xiao, M. A. Bruck, J. H. Enemark, C. G. Young, A. G.
Wedd, Inorg. Chem. 1996, 35, 7508–7515.
[4] A. A. Eagle, S. M. Harben, E. R. T. Tiekink, C. G. Young, J.
Am. Chem. Soc. 1994, 116, 9749–9750.
[5] R. H. Holm, Chem. Rev. 1987, 87, 1401–1449 and references
cited therein.
[6] J. Topics, J. T. Lyon III, Inorg. Chem. 1984, 23, 3202–3206.
[7] a) S. Bhattacharyya, R. Bhattacharyya, J. Chem. Soc., Dalton
Trans. 1992, 1357–1364; b) S. Bhattacharyya, R. Bhattach-
aryya, J. Chem. Soc., Dalton Trans. 1993, 1151–1158.
[8] S. K. Das, P. K. Chaudhury, D. Biswas, S. Sarkar, J. Am. Chem.
Soc. 1994, 116, 9061–9070.
a) A. Goti, M. Romani, Tetrahedron Lett. 1994, 35, 6567–6570;
b) R. W. Murray, K. Iyanar, J. Chen, J. T. Wearing, Tetrahedron
Lett. 1996, 37, 805–808; c) A. Goti, M. Romani, Tetrahedron
Lett. 1996, 37, 6025–6028; d) K. Yamaguchi, N. Mizuno, An-
gew. Chem. Int. Ed. 2003, 42, 1480–1483.
S. E. Jacobson, D. A. Muccigrosso, F. Mares, J. Org. Chem.
1979, 44, 921–924.
a) B. M. Trost, Y. Masuyama, Isr. J. Chem. 1984, 24, 134; b)
B. M. Trost, Y. Masuyama, Tetrahedron Lett. 1984, 25, 173–
176.
a) A. Arcoria, F. P. Ballistreri, G. A. Tomaselli, F. Di Furia, G.
Modena, J. Org. Chem. 1986, 51, 2374–2376; b) O. Bartolini,
V. Conte, F. Di Furia, G. Modena, J. Org. Chem. 1986, 51,
[24]
[25]
[26]
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