Prices for PMHS from ABCR, Alfa, Aldrich, Lancaster, vary
between €2–6 per mol; PMHS is available in forms differing in the
molecular mass range of the polymer. Whilst the reactivity of the
different forms is unlikely to vary greatly, the differences in viscosity
could have important implications for their ease of handling in a
reaction and subsequent work-up .
LD50 80 g kg–1. A. L. Klyaschitskaya, G. N. Krasovskii and S. A. Fridlyand, Gig. Sanit., 1970, 35, 28 (Chem. Abstr., 1970, 72, 124864r) Search PubMed.
In vitro IC50(Chinese hamster lung fibroblast V79 cells) 2700 µg ml–1 Y. Ikarashi, T. Tsuchiya and A. Nakamura, J. Toxicol., Cutaneous Ocul. Toxicol., 1993, 12, 15 Search PubMed.
R. O. Sauer, W. J. Scheiber and S. D. Brewer, J. Am. Chem. Soc., 1946, 68, 962 CrossRefCAS.
The synthetic applications of PMHS have previously been reviewed. See J. Lipowitz and S. A. Bowman, Aldrichimica Acta, 1973, 6, 1 Search PubMed.
K. Hayashi, J. Iyoda and I. Shiihara, J. Organomet. Chem., 1967, 10, 81 CrossRefCAS.
H. Deleuze and B. Maillard, J. Organomet. Chem., 1995, 490, C14 CrossRefCAS.
D. S. Hays and G. C. Fu, J. Org. Chem., 1997, 62, 7070 CrossRefCAS.
J. Light and R. Breslow, Tetrahedron Lett., 1990, 31, 2957 CrossRefCAS.
S. A. Matlin and P. S. Gandham, J. Chem. Soc., Chem. Commun., 1984, 798 RSC.
R. J. Sundberg and R. J. Cherney, J. Org. Chem., 1990, 55, 6028 CrossRefCAS; D. Batty, D. Crich and S. M. Fortt, J. Chem. Soc., Perkin Trans. 1, 1990, 2875 RSC; J. M. Denner and D. J. Hart, Tetrahedron, 1988, 44, 7037 CrossRef; W. H. Pearson, A. C. Lindbeck and J. W. Kampf, J. Am. Chem. Soc., 1993, 115, 622 ; W. R. Roush and B. B. Brown, J. Am. Chem. Soc., 1993, 115, 2268 CrossRefCAS; C. R. Johnson and J. R. Medich, J. Org. Chem., 1988, 53, 4131 CrossRefCAS; Y. I. M. Nilsson, A. Aranyos, P. G. Andersson, J. E. Backvall, J. L. Parrain, C. Ploteau and J. P. Quintard, J. Org. Chem., 1996, 61, 1825 CrossRefCAS; A. Philippon, J. C. Tao, D. Tetard, M. Degueil Castaing and B. Maillard, Synth. Commun., 1997, 27, 2651 CAS; A. M. Horneman and I. Lundt, Tetrahedron, 1997, 53, 6879 CrossRefCAS; M. Newcomb, O. M. Musa, F. N. Martinez and J. H. Horner, J. Am. Chem. Soc., 1997, 119, 4569 CrossRefCAS; P. Four and F. Guibé, J. Org. Chem., 1981, 46, 4439 CrossRefCAS; P. Kocienski and C. Pant, Carbohydr. Res., 1982, 11, 330 CrossRefCAS For uses of dibutyltin dihydride from Bu2 SnO–PMHS see H. E. Ensley, R. R. Buescher and K. Lee, J. Org. Chem., 1982, 47, 404 Search PubMed; B. Jousseaume, N. Noiret, M. Pereyre, A. Saux and J. M. Francis, Organometallics, 1994, 13, 1034 CrossRefCAS.
T. V. Rajan Babu,
in Encyclopedia of Reagents for Organic Synthesis,
ed. L. A. Paquette,
Wiley,
New York,
1995 Search PubMed; P. Neumann, Synthesis, 1987, 665 Search PubMed.
P. G. M. Wuts, R. D'Costa and W. Butler, J. Org. Chem., 1984, 49, 2582 CrossRefCAS.
G. L. Grady and H. G. Kuivila, J. Org. Chem., 1969, 34, 2014 CrossRefCAS.
M. Grignon-Dubois and J. Dunogues, J. Organomet. Chem., 1986, 309, 35 CrossRefCAS.
N. O. Brace, J. Fluorine Chem., 1982, 20, 313 CrossRefCAS.
G. L. Grady and S. K. Chokshi, Synthesis, 1972, 483 CrossRefCAS.
M. Maeda, M. Abe and M. Kojima, J. Fluorine Chem., 1987, 34, 337 CrossRefCAS.
D. A. Eppstein, Y. V. Marsh, B. B. Schryver, M. A. Larsen, J. W. Barnett, J. P. H. Verheyden and E. J. Prisbe, J. Biol. Chem., 1982, 257, 13390 CAS.
R. J. Conway, J. P. Nagel, R. V. Stick and D. M. G. Tilbrook, Aust. J. Chem., 1985, 38, 939 CAS.
E. J. Prisbe and J. C. Martin, Synth. Commun., 1985, 15, 401 CAS.
G. V. B. Madhavan and J. C. Martin, J. Org. Chem., 1986, 51, 1287 CrossRefCAS.
H. Kawakami, T. Ebata, K. Koseki, K. Okano, K. Matsumoto and H. Matsushita, Heterocycles, 1993, 36, 2765 CAS.
M. Sekine and T. Satoh, J. Org. Chem., 1991, 56, 1224 CrossRefCAS.
Y. Ueno and M. Okawara, J. Am. Chem. Soc., 1979, 101, 1893 CrossRefCAS.
H. G. Kuivila and L. W. Menapace, J. Org. Chem., 1963, 28, 2165 CAS.
I. J. Boyer, Toxicology, 1989, 55, 253 CrossRefCAS.
S. Nitzsche and M. Wick, Angew. Chem., 1957, 69, 96 CAS.
S. Nitzsche and
M. Wick,
Ger. Pat. 1 079 600, Apr 14,
1960;
Chem. Abstr.,
1961,
55,
19861h;
US Pat. 3 061 424,
1962 Search PubMed.
J. Lipowitz and S. A. Bowman, J. Org. Chem., 1973, 38, 162 CrossRefCAS.
K. Itoi and S. Kumano, Kogyo Kagaku Zasshi, 1967, 70, 82 CAS.
M. Pereyre and J. Godot, Tetrahedron Lett., 1970, 11, 3653 CrossRef.
A. K. Sawyer and H. G. Kuivila, J. Org. Chem., 1962, 27, 613 .
H. G. Kuivila and O. F. Beumal, Jr., J. Am. Chem. Soc., 1961, 83, 1246 CrossRefCAS.
K. Itoi,
Fr. Pat. 1 368 522, 1964; see also ref. 32 .
D. S. Hays and G. C. Fu, J. Org. Chem., 1996, 61, 4 CrossRefCAS.
D. S. Hays, M. Scholl and G. C. Fu, J. Org. Chem., 1996, 61, 6751 CrossRefCAS.
R. M. Lopez and G. C. Fu, Tetrahedron, 1997, 53, 16349 CrossRefCAS.
R. M. Lopez, D. S. Hays and G. C. Fu, J. Am. Chem. Soc., 1997, 119, 6949 CrossRefCAS.
for a review of methods for the radical deoxygenation of alcohols see W. Hartwig, Tetrahedron, 1983, 39, 2609 Search PubMed.
D. S. Hays and G. C. Fu, J. Org. Chem., 1998, 63, 2796 CrossRefCAS.
R. E. Maleczka, Jr. and I. Terstiege, J. Org. Chem., 1998, 63, 9622 CrossRef.
I. Terstiege and R. E. Maleczka, Jr., J. Org. Chem., 1999, 64, 342 CrossRefCAS.
S. C. Berk, K. A. Kreutzer and S. L. Buchwald, J. Am. Chem. Soc., 1991, 113, 5093 CrossRefCAS.
S. Xin, C. Aitken, J. F. Harrod, Y. Mu and E. Samuel, Can. J. Chem., 1990, 68, 471 CAS.
MSDS for SiH4 and CH3 SiH3: Voltaix, Inc., PO Box 5357,
N. Branch, NJ 08876, USA; http://www.voltaix.com/msds/nch3sih3.htm .
R. M. Laine, J. A. Rahn, K. A. Yoiungdahl, F. Babonneau, M. L. Hoppe, Z.-F. Zhang and J. F. Harrod, Chem. Mater., 1990, 2, 464 CrossRefCAS.
H.-G. Woo and T. D. Tilley, J. Am. Chem. Soc., 1989, 111, 3757 CrossRefCAS; H.-G. Woo and T. D. Tilley, J. Am. Chem. Soc., 1989, 111, 8043 CrossRefCAS.
A. Albizzati, L. Abis, E. Pettenati and E. Giannetti, Inorg. Chim. Acta, 1986, 120, 197 CrossRef.
K. J. Barr, S. C. Berk and S. L. Buchwald, J. Org. Chem., 1994, 59, 4323 CrossRefCAS.
S. C. Berk and S. L. Buchwald, J. Org. Chem., 1992, 57, 3751 CrossRef.
T. Coumbe, N. J. Lawrence and F. Muhammad, Tetrahedron Lett., 1994, 35, 625 CrossRefCAS.
J. C. Briggs, C. A. McAuliffe, W. E. Hill, D. M. A. Minahan, J. G. Taylor and G. Dyer, Inorg. Chem., 1982, 21, 4204 CrossRefCAS.
H. Fritzsche, U. Hasserodt and F. Korte, Chem. Ber., 1964, 97, 1988 CAS.
H. Fritzsche, U. Hasserodt and F. Korte, Chem. Ber., 1965, 98, 1681 .
S. Warren and P. Wyatt, Tetrahedron: Asymmetry, 1996, 7, 989 CrossRefCAS.
S. Warren and P. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1998, 249 RSC.
M. G. Russell and S. Warren, Tetrahedron Lett., 1998, 39, 7995 CrossRefCAS.
N. J. Lawrence and F. Muhammad, Tetrahedron, 1998, 54, 15361 CrossRefCAS.
N. J. Lawrence and H. Beynek, Synlett, 1998, 497 CAS.
A. Arin, A. J. Blake, W.-S. Li and N. S. Simpkins, Synlett, 1997, 1453 CAS.
Y. Hamada, F. Matsuura, M. Oku, K. Hatano and T. Shiori, Tetrahedron Lett., 1997, 38, 8961 CrossRefCAS.
S. W. Breeden and N. J. Lawrence, Synlett, 1994, 833 CrossRefCAS.
M. T. Reding and S. L. Buchwald, J. Org. Chem., 1995, 60, 7884 CrossRefCAS.
X. Verdaguer, S. C. Berk and S. L. Buchwald, J. Am. Chem. Soc., 1995, 117, 12641 CrossRefCAS.
X. Verdaguer, M. C. Hansen, S. C. Berk and S. L. Buchwald, J. Org. Chem., 1997, 62, 8522 CrossRefCAS.
M. C. Hansen, X. Verdaguer and S. L. Buchwald, J. Org. Chem., 1998, 63, 2360 CrossRefCAS.
R. L. Halterman, T. M. Ramsey and Z. L. Chen, J. Org. Chem., 1994, 59, 2642 CrossRefCAS.
M. B. Carter, B. Schiøtt, A. Gutiérrez and S. L. Buchwald, J. Am. Chem. Soc., 1994, 116, 11667 CrossRefCAS.
X. Verdaguer, U. E. W. Lange and S. L. Buchwald, Angew. Chem., Int. Ed., 1998, 37, 1103 CrossRefCAS.
M. C. Hansen and S. L. Buchwald, Tetrahedron Lett., 1999, 40, 2033 CrossRefCAS.
C. Chuit, R. J. P. Corriu, C. Rey and J. C. Young, Chem. Rev., 1993, 93, 1371 CrossRefCAS.
C. Chuit, R. J. P. Corriu, R. Perz and C. Reyé, Synthesis, 1982, 981 CrossRefCAS.
(a) J. Boyer, R. J. P. Corriu, R. Perz and C. Reyé, Tetrahedron, 1981, 37, 2165 CrossRefCAS;
(b) J. Boyer, R. J. P. Corriu, R. Perz and C. Reyé, J. Chem. Soc., Chem. Commun., 1981, 121 RSC;
(c) R. J. P. Corriu, R. Perz and C. Reyé, Tetrahedron, 1983, 39, 999 CrossRefCAS.
J. Boyer, R. J. P. Corriu, R. Perz, M. Poirier and C. Reyé, Synthesis, 1981, 558 CrossRefCAS.
M. Drew and N. J. Lawrence, Abstracts of Papers of the American Chemical Society, 1996, 212 Search PubMed 059-ORGN later followed by M. D. Drew, N. J. Lawrence, D. Fontaine, L. Sehkri, W. Watson and S. A. Bowles, Synlett, 1997, 989 Search PubMed.
Y. Kobayashi, E. Takahisi, M. Nakano and K. Watatani, Tetrahedron, 1997, 53, 1627 CrossRef.
Triton® B 500 cm3 of a 40%(w/v) solution in methanol, £22.50.
Cost per mole of nucleophile: £19. TBAF, 100 g of the monohydrate, £126.20. Cost per mole of nucleophile: £330; Aldrich Chemical Co., UK,
1999/2000 .
M. D. Drew, N. J. Lawrence, W. Watson and S. A. Bowles, Tetrahedron Lett., 1997, 38, 5857 CrossRefCAS.
Y. Yoshimura, T. Ueda and A. Matsuda, Tetrahedron Lett., 1991, 32, 4549 CrossRefCAS; Y. Yoshimura, B. A. Otter, T. Ueda and A. Matsuda, Chem. Pharm. Bull., 1992, 40, 1761 CAS.
G. T. Brooks, A. P. Ottridge, R. C. Jennings, D. W. Mace and B. A. Alexander, Pest. Sci., 1985, 16, 571 Search PubMed.
L. R. Subramanian, A. G. Martinez, A. H. Fernandez and R. M. Alvarez, Synthesis, 1984, 481 CrossRefCAS.
I. Pri-Bar and O. Buchman, J. Org. Chem., 1986, 51, 734 CrossRefCAS.
I. Pri-Bar and O. Buchman, J. Org. Chem., 1984, 49, 4009 CrossRef.
E. Keinan and N. Greenspoon, J. Org. Chem., 1983, 48, 3545 CrossRefCAS; E. Keinan and N. Greenspoon, Israel J. Chem., 1984, 24, 82 Search PubMed.
E. Keinan and P. A. Gleize, Tetrahedron Lett., 1982, 23, 241 CrossRefCAS.
E. Keinan and N. Greenspoon, Tetrahedron Lett., 1982, 23, 477 CrossRefCAS.
R. Braden and T. Himmler, J. Organomet. Chem., 1989, 367, C12 CrossRefCAS.
J. Blum, I. Pri-Bar and H. Alper, J. Mol. Catal., 1986, 37, 359 CrossRefCAS.
J. Blum, G. Bitan, S. Marx and K. P. C. Vollhardt, J. Mol. Catal., 1991, 66, 313 CrossRefCAS.
H. Mimoun, J. Org. Chem., 1999, 64, 2582 CrossRefCAS; H. Mimoun,
Fr. Pat.,
1996,
WO96/12694;
Chem. Abstr.,
1997,
125,
114173 Search PubMed.
Trademark of Morton International, Inc .
H. Mimoun, J. Y. Saint de Laumer, L. Giannini, R. Scopelliti and C. Floriani, J. Am. Chem. Soc., 1999, 121, 6158 CrossRefCAS We thank Professor Mimoun for a pre-print of this paper.
S. Chandrasekhar, Y. R. Reddy and C. Ramarao, Synth. Commun., 1997, 27, 2251 CrossRefCAS.
S. Chandrasekhar, Y. R. Reddy and Ch. R. Reddy, Chem. Lett., 1998, 1273 CAS.
J. M. Aizpurua, B. Lecea and C. Palomo, Can. J. Chem., 1986, 64, 2342 CAS.
A. Jaxa-Chamiec, V. P. Shah and L. I. Kruse, J. Chem. Soc., Perkin Trans. 1, 1989, 1705 RSC.
J. Hawari, J. Organomet. Chem., 1992, 437, 91 CrossRefCAS.
D. Griller,
J. A. Hawari and
D. J. McPhee,
US Pat. 4 973 783,
27 Nov, 1990;
Chem. Abstr.,
1991,
114,
142845a Search PubMed.
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