DOI: 10.1016/s0022-328x(00)00765-8. Synthesis and reactivity of subvalent compounds

Synthesis and reactivity of subvalent compounds

10.1016/s0022-328x(00)00765-8

Crossref journal-article

Elsevier BV

Journal of Organometallic Chemistry (78)

Bibliography

Denk, M. K., & Rodezno, J. M. (2001). Synthesis and reactivity of subvalent compounds. Journal of Organometallic Chemistry, 617â618, 737â740.

Authors 2

Michael K. Denk (first)
José M. Rodezno (additional)

References 13 Referenced 29

(a) A. Igau, H. Grützmacher, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 110 (1988) 6463. (b) L. Nyulaszi, D. Szieberth, J. Reffy, T. Veszpremi, Theochem. J. Mol. Struct. 453 (1998) 91. (c) D. Bourissou, O. Guerret, F.P. Gabbai, G. Bertrand, Chem. Rev. 100 (2000) 39. (d) C. Buron, H. Gornitzka, V. Romanenko, G. Bertrand, Science 288 (2000) 834. (10.1021/ja00227a028)
(a) A.J. Arduengo, R.L. Harlow, M. Kline, J. Am. Chem. Soc. 113 (1991) 361. (b) A.J. Arduengo, H.V.R. Dias, R.L. Harlow, M. Kline, J. Am. Chem. Soc. 114 (1992), 5530. (c) A.J. Arduengo, J. Goerlich, W. Marshall, J. Am. Chem. Soc. 117 (1995) 11 027. (d) A.J. Arduengo, F. Davidson, H.V.R. Dias, J.R. Goerlich, D. Khasnis, W.J. Marshall, T.K. Prakasha, J. Am. Chem. Soc. 119 (1997) 12 742. (10.1021/ja00001a054)
R.W. Alder, M.E. Blake, C. Bortolotti, S. Bufali, C.P. Butts, E. Linehan, J.M. Oliva, A.G. Orpen, M.J. Quayle, J. Chem. Soc. Chem. Commun. (1999) 241. (10.1039/a808951e)
(a) M.K. Denk, K. Hatano, M.J. Ma, Tetrahedron Lett. 40 (1999) 2057. (b) J.F. Lehmann, S.G. Urquhart, L.E. Ennis, A. Hitchcock, K. Hatano, S. Gupta, M.K. Denk, Organometallics 18 (1999) 1862. (c) M.K. Denk, A. Thadani, K. Hatano, A.J. Lough, Angew. Chem. Int. Ed. Engl. 36 (1997) 2607; Angew. Chem. 109 (1997) 2719. (10.1016/S0040-4039(99)00164-1)
(a) M. Haaf, A. Schmiedl, T.A. Schmedake, R.A. Powell, A.J. Millevolte, M. Denk, R. West, J. Am. Chem. Soc. 120 (1998) 12 714. (b) S. Urquhart, A.P. Hitchcock, M.K. Denk, Organometallics 17 (1998) 2352. (c) M.K. Denk, K. Hatano, A.J. Lough, Eur. J. Inorg. Chem. (1998) 1067. (d) N. Metzler, M.K. Denk, J. Chem. Soc. Chem. Commun. (1996) 2657. (e) R. West, M. Denk, Pure Appl. Chem. 68 (1996) 785. (f) M. Denk, J.C. Green, N. Metzler, M. Wagner, J. Chem. Soc. Dalton Trans. (1994) 2405. (g) M. Denk, R.K. Hayashi, R. West, J. Chem. Soc. Chem. Commun. (1994) 33. (h) M. Denk, R. Lennon, R. Hayashi, R. West, A. Haaland, A.V. Belyakov, H.P. Verne, M. Wagner, N. Metzler, J. Am. Chem. Soc. 116 (1994) 2691. (i) M. Denk, R.K. Hayashi, R. West, J. Am. Chem. Soc. 116 (1994) 10 813. (j) A.J. Arduengo, H. Bock, H. Chen, M. Denk, D.A. Dixon, J.C. Green, W.A. Herrmann, N.L. Jones, M. Wagner, R. West, J. Am. Chem. Soc. 116 (1994) 6641. (10.1021/ja00094a020)
(a) W.A. Herrmann, M. Denk, J. Behm, W. Scherer, F.-R. Klingan, H. Bock, B. Solouki, M. Wagner, Angew. Chem. 104 (1992) 1489; Angew. Chem. Int. Ed. Engl. 31 (1992) 1485. (b) M.K. Denk, M. Khan, A.J. Lough, K. Shuchi, Acta Crystallogr. Sect C 54 (1998) 1830. (10.1002/anie.199214851)
(a) M.K. Denk, S. Gupta, R. Ramachandran, Eur. J. Inorg. Chem. (1999) 41. (b) M.K. Denk, S. Gupta, R. Ramachandran, Tetrahedron Lett. (1996) 9025. (10.1002/(SICI)1099-0682(199901)1999:1<41::AID-EJIC41>3.0.CO;2-#)
For a discussion of oxygen transfer reactions and their reaction energies see: R.H. Holm, J.P. Donahue, Polyhedron 12 (1993) 571 (Polyhedron Special Report 45). (10.1016/S0277-5387(00)84972-4)
R. Oda, M. Mieno, Y. Hayashi, Tetrahedron Lett. 25 (1967) 2363. (10.1016/S0040-4039(00)71607-8)
The protonation of stable carbenes at the carbene carbon atom has been previously investigated through calculations: (a) D.A. Dixon, A.J. Arduengo, J. Phys. Chem. 95 (1991) 4180. (b) R.W. Alder, M.E. Blake, J.M. Oliva, J. Phys. Chem. Sect. A 103 (1999) 11 200. (10.1021/j100164a003)
For the experimental generation of a diaminocarbene dication see: G.A. McGibbon, C. Heinemann, D.J. Lavorato, H. Schwarz, Angew. Chem. Int. Ed. Engl. 36 (1997) 1478. (10.1002/anie.199714781)
The calculations were carried out with the spartan-5.02 and gaussian-94 suite of programs: gaussian-94, Revision D.4, M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, and J.A. Pople, Gaussian, Inc., Pittsburgh PA, 1995. Molecular geometries were fully optimized and vibrational frequencies were calculated as indicated. The absence of virtual frequencies ensures that the calculated structures are minima rather than saddle points. Zero point vibrational energies: (b) J.B. Foresman, A. Frisch, Exploring Chemistry with Electronic Structure Methods, second ed., Gaussian Inc., Pittsburgh, PA, 1996. (c) I. Bytheway, M.W. Wong, Chem. Phys. Lett. 282 (1998) 219. (d) A.P. Scott, L. Radom, J. Phys. Chem. 100 (1996) 16 502.
The imidazolium salt [4]+Cl− was prepared from tert-butyl amine, glyoxal, and formaldehyde following the procedure in Ref. [2a]. X-ray quality crystals of [4]+Cl− were grown by slow evaporation of a concentrated aqueous solution. Monoclinic, space group P21/n, a=9.036(1), b=12.0229(1), c=11.341(1) Å; α=γ=90, β=95.78°, volume=1225.7(4) Å3, Z=4, Dcalc.=1.175 g cm−3, 4.37≤θ≤23.02°, total reflections 6315, independent reflections 1695 (Rint=0.1140), scaleback absorption correction, refinement full-matrix least squares on F2, Goodness-of-fit=1.057, R1 =0.0697, largest difference peak and hole +0.360 and −0.264 e Å−3.

Dates

Type	When
Created	23 years, 1 month ago (July 25, 2002, 11:12 a.m.)
Deposited	5 years, 7 months ago (Jan. 14, 2020, 5:13 p.m.)
Indexed	4 months, 1 week ago (April 29, 2025, 6:02 p.m.)
Issued	24 years, 8 months ago (Jan. 1, 2001)
Published	24 years, 8 months ago (Jan. 1, 2001)
Published Print	24 years, 8 months ago (Jan. 1, 2001)

Funders 0

None

BibTeX

@article{Denk_2001, title={Synthesis and reactivity of subvalent compounds}, volume={617–618}, ISSN={0022-328X}, url={http://dx.doi.org/10.1016/s0022-328x(00)00765-8}, DOI={10.1016/s0022-328x(00)00765-8}, journal={Journal of Organometallic Chemistry}, publisher={Elsevier BV}, author={Denk, Michael K. and Rodezno, José M.}, year={2001}, month=jan, pages={737–740} }

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