Abstract
Organotin compounds find a bigger range of technological and industrial applications than the organic compounds of any other metal. Many of these applications involve catalysis or anticatalysis, often in polymer chemistry, and they have an importance out of all proportion to the tonnage of tin which is used. This article reviews the present standing of the non-biological applications of organostannanes, with an emphasis on the mechanisms of the reactions which are involved.
References
1.
Hoch M.
, Appl. Geochem. , 2001 , 16 , 719 .
2.
Champ M.A.
, Sci. Total Environ. , 2000 , 258 , 21 .
3.
Blunden S.J.
,
Cusack P. A.
, and
Hill R.
, Industrial uses of tin chemicals , The Royal Society of Chemistry , London , 1985 .
4.
Evans C.J.
, and
Karpel S.
, Organotin compounds in modern technology , Elsevier , Amsterdam , 1985 .
5.
Evans C.J.
, Chemistry of tin , ed.
Smith P. J.
, Blackie , London , 2nd edn, 1998 , pp. 442 –479 .
6.
Omae I.
, Applications of organometallic compounds , Wiley , Chichester , 1998 .
7.
Davies A.G.
, Organotin chemistry , 2 edn, Wiley-VCH , Weinheim , 2004 .
8.
Davies A.G.
, J. Chem. Res. , 2004 , 309 .
9.
Hutton R.E.
,
Burley J. W.
, and
Oakes V.
, J. Organomet. Chem. , 1978 , 156 , 369 .
10.
Burley J.W.
,
Hutton R. E.
, and
Oakes V.
, J. Organomet. Chem. , 1978 , 156 , 369 .
11.
Burley J.W.
,
Hope P.
,
Hutton R. E.
, and
Groenenboom C. J.
, J. Organomet. Chem. , 1979 , 170 , 21 .
12.
Wilkes C.E.
,
Summers J. W.
, and
Daniels C. A.
, eds., PVC Handbook , Hanser , Munich , 2005 .
13.
Endo K.
, Progr. Polym. Sci. , 2002 , 27 , 2021 .
14.
US Patent 2,219,463, 1940 .
15.
Thacker G.A.
, in Handbook of vinyl formulating , 2nd edn, ed.
Grossman R. F.
, Wiley , Hoboken , 2008 , pp. 503 .
16.
Frye A.H.
,
Host R. W.
, and
Paliobagis M. A.
, J. Polym. Sci. A , 1964 , 2 , 1765 .
17.
Frye A.H.
,
Host R. W.
, and
Paliobagis M. A.
, J. Polym. Sci. A , 1964 , 2 , 1785 .
18.
Frye A.H.
,
Host R. W.
, and
Paliobagis M. A.
, J. Polym. Sci. A , 1964 , 2 , 1801 .
19.
Poller R.C.
, J. Macromol. Sci. Chem. , 1978 , 12A , 373 .
20.
Arkis E.
, and
Balkoese D.
, Polym. Degrad. Stab. , 2005 , 88 , 46 .
21.
Ulrich H.
, in Encyclopedia of chemical technology , Wiley , New York , 1997 , vol. 24 , pp. 695 –726 .
22.
Wicks D.A.
, and
Wicks Z. W.
, Progr. Org. Coat. , 1999 , 36 , 137 .
23.
Bloodworth A.J.
, and
Davies A. G.
, Proc. Chem. Soc. , 1963 , 264 .
24.
Bloodworth A.J.
, and
Davies A. G.
, J. Chem. Soc. , 1965 , 5238 .
25.
Jousseaume B.
,
Laporte C.
,
Toupance T.
, and
Bernard J. M.
, Tetrahedron Lett. , 2003 , 44 , 5983 .
26.
Jousseaume B.
,
Noiret N.
,
Pereyre M.
, and
Saux A.
, Organometallics , 1994 , 13 , 1034 .
27.
Nomura Y.
,
Sato S.
,
Mor H.
, and
Endo T.
, J. Appl. Polym. Sci. , 2008 , 100 , 608 .
28.
Van der Weij F.W.
, Makromol. Chem. , 1980 , 181 , 2541 .
29.
Otera J.
,
Dan-oh N.
, and
Nozaki H.
, J. Org. Chem. , 1991 , 56 , 5307 .
30.
Otera J.
, Adv. Detail. React. Mech. , 1994 , 3 , 167 .
31.
Crawford E.
,
Lohr T.
,
Leitao E. M.
,
Kwok S.
, and
McIndoe J. S.
, Dalton Trans. , 2009 , 9110 .
32.
Shyamroy S.
,
Garnaik B.
, and
Sivaram S.
, J. Polymer Sci. A , 2005 43 , 2164 .
33.
Chrétien J.-M.
,
Zammattio F.
,
Grognec E. L.
,
Paris M.
,
Cahingt B.
,
Montavon G.
, and
Quintard J.-P.
, J. Org. Chem. , 2005 , 70 , 2870 .
34.
Otera J.
, Acc. Chem. Res. , 2004 , 37 , 288 .
35.
An D.L.
,
Peng Z.
,
Orita A.
,
Kurita A.
,
Mane S.
,
Ohkubo K.
,
Li X.
,
Fukuzumi S.
, and
Otera J.
, Chem., Eur. J. , 2006 , 1642 .
36.
Otera J.
,
Biesemans M.
,
Pinoie V.
,
Poelmans K.
, and
Willem R.
, in Tin Chemistry. fundamentals, frontiers, and applications , eds
Davies A. G.
,
Gielen M.
,
Pannell K. H.
, and
Kiekink E. R. T.
, Wiley , Chichester , 2008 , pp. 680 –667 .
37.
Yean C.H.
, and
Das V. G. K.
, Appl. Organometal. Chem. , 2000 , 14 , 304 .
38.
US Patent 2,720,507, 1955 .
39.
GB Patent 935,740, 1963.
40.
Dannoux M.
,
Cassagnau P.
, and
Michel A.
, Can. J. Chem. Eng. , 2002 , 80 , 1075 .
41.
Saint-Loup R.
,
Jeanmaire T.
,
Robin J.-J.
, and
Boutevin B.
, Polymer , 2003 , 44 , 3437 .
42.
Youk J.H.
,
Boulares A.
,
Kambour R. P.
, and
MacKnight W. J.
, Macromolecules , 2000 , 32 , 3600 .
43.
Kricheldorf H.R.
,
Stricker A.
, and
Langanke D.
, Macromol. Chem. Phys. , 2001 , 202 , 2963 .
44.
Kricheldorf H.R.
,
Probst N.
,
Langanke D.
, and
Schwarz G.
, Macromol. Rapid Commun. , 2001 , 87 , 750 .
45.
Mascaretti O.A.
, and
Furlán R. L. E.
, Aldrichimica Acta , 1997 , 30 , 55 .
46.
Deshayes G.
,
Mercier F. A. G.
,
Degée P.
,
Verbruggen I.
,
Biesemans M.
,
Willem R.
, and
Dubois P.
, Chem. Eur. J. , 2003 , 4346 .
47.
Jousseaume B.
,
Laporte C.
,
Rascle M.-C.
, and
Toupance T.
, Chem. Commun. , 2003 , 1428 .
48.
Choi J.-C.
,
He L.-N.
,
Yasuda H.
, and
Sakakura T.
, Green Chem. , 2002 , 4 , 230 .
49.
Ballivet-Tkatchenko D.
,
Chambrey S.
,
Keiski R.
,
Ligabue R.
,
Plasseraud L.
,
Richard P.
, and
Turunen H.
, Catal. Today , 2006 , 115 , 80 .
50.
Allendorf M.D.
, Interface , 2001 , 34 .
51.
van Mol A.M. B.
,
Chae Y.
,
McDaniel A. H.
, and
Allendorf M. D.
, Thin Solid Films , 2006 , 502 , 72 .
52.
Molloy K.
, J. Chem. Res. , 2008 , 549 .
53.
Giunta C.J.
,
Strickler D. A.
, and
Gordon R. G.
, J. Phys. Chem. , 1993 , 97 , 2275 .
54.
Chae Y.
,
Houf W. G.
,
McDaniel A. H.
, and
Allendorf M. D.
, J. Electrochem. Soc. , 2006 , 153 , C309 .
55.
de Mora S.J.
, ed., Tributyltin: case study of an environmental contaminant , Cambridge University Press , Cambridge , 1996 .
56.
de Mora S.J.
, in Tributyltin: Case study of an environmental contaminant , ed.
de Mora S. J.
, Cambridge University Press , Cambridge , 1996 , pp. 1 –20 .
