How Not to Discover a New
Reagent. The Evolution and Chemistry of Woollins’ Reagent

J. Derek Woollins

doi:10.1055/s-0031-1290665

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Synlett 2012(8): 1154-1169
DOI: 10.1055/s-0031-1290665

ACCOUNT

How Not to Discover a New Reagent. The Evolution and Chemistry of Woollins’ Reagent

J. Derek Woollins*
EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
Fax: 44(1334)463384; e-Mail: jdw3@st-and.ac.uk;

Further Information

Publication History

Received 21 November 2011
Publication Date:
26 April 2012 (online)

Abstract
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Abstract

The pathways in research can be complex. This review provides a personal account of the winding scientific and funding road that led to Woollins’ reagent. The synthesis and applications of Woollins’ reagent are summarised.

Key words

heterocycles - phosphorus - selenium - group 16

References

1 Goehring M. Debo A. Z. Anorg. Allg. Chem. 1953, 273: 319

Google Scholar
2 Daum KW. Goehring M. Weiss J. Z. Anorg. Allg. Chem. 1955, 278: 260

Google Scholar
3 Piper TS. J. Am. Chem. Soc. 1958, 80: 30

Google Scholar
4 Woollins JD. Grinter R. Johnson MK. Thomson AJ. J. Chem. Soc., Dalton Trans. 1980, 1910

Google Scholar
5 Powell DB. Woollins JD. Spectrochim. Acta, Part A 1980, 36: 447

Google Scholar
6a Ghosh AK. Bilcer G. Schiltz G. Synthesis 2001, 2203

Google Scholar
6b List B. Castello C. Synlett 2001, 1687

Google Scholar
7 Irgolic KJ. In Houben-Weyl 4th ed., Vol. E12b: Klamann D. Thieme; Stuttgart: 1990. p.150

Google Scholar
8 For a review, see: Labes MM. Love P. Nichols LF. Chem. Rev. 1979, 79: 1

Google Scholar
9 Chivers T. Chem. Rev. 1985, 85: 341

Google Scholar
10 Chivers T. A Guide to Chalcogen-Nitrogen Chemistry World Scientific; Singapore: 2005.

Google Scholar
11a Morris JL. Rees CW. Chem. Soc. Rev. 1986, 1

Google Scholar
11b Rees CW. J. Heterocycl. Chem. 1992, 29: 639

Google Scholar
12 Nikonov GN. Balueva AS. In Comprehensive Heterocyclic Chemistry II Vol. 9: Katritsky AR. Rees CW. Scriven EFV. Newkome GR. Pergamon/Elsevier; Oxford: 1996.

Google Scholar
13 Kelly PF. Woollins JD. Polyhedron 1986, 5: 607

Google Scholar
14 Chivers T. Edelmann F. Polyhedron 1986, 5: 1661

Google Scholar
15 Kelly PF. Slawin AMZ. Williams DJ. Woollins JD. Chem. Soc. Rev. 1992, 246

Google Scholar
16a Jones R. Kelly PF. Warrens CP. Williams DJ. Woollins JD. J. Chem. Soc., Chem. Comm. 1986, 711

Google Scholar
16b Jones R. Warrens CP. Williams DJ. Woollins JD. J. Chem. Soc., Dalton Trans. 1987, 907

Google Scholar
16c Jones R. Kelly PF. Williams DJ. Woollins JD. J. Chem. Soc., Dalton Trans. 1988, 803

Google Scholar
17a Kelly PF. Slawin AMZ. Williams DJ. Woollins JD. J. Chem. Soc., Chem. Commun. 1989, 408

Google Scholar
17b Kelly PF. Parkin IP. Slawin AMZ. Williams DJ. Woollins JD. Angew. Chem. Int. Ed. Engl. 1989, 28: 1047

Google Scholar
17c Kelly PF. Slawin AMZ. Williams DJ. Woollins JD. Polyhedron 1990, 9: 1567

Google Scholar
18 Kelly PF. Slawin AMZ. Williams DJ. Woollins JD. Angew. Chem. Int. Ed. Engl. 1992, 31: 616

Google Scholar
19a Kelly PF. Slawin AMZ. Williams DJ. Woollins JD. Polyhedron 1991, 10: 2337

Google Scholar
19b Ginn VC. Kelly PF. Slawin AMZ. Williams DJ. Woollins JD. J. Chem. Soc., Dalton Trans. 1992, 963

Google Scholar
20 Roesky HW. Rao MNS. Nakajima T. Sheldrick WS. Chem. Ber. 1979, 112: 3351

Google Scholar
21 Belton PS. Ginn VC. Kelly PF. Woollins JD.
J. Chem. Soc., Dalton Trans. 1992, 1135

Google Scholar
22 Menzer S. Phillips JR. Slawin AMZ. Williams DJ. Woollins JD. J. Chem. Soc., Dalton Trans. 2000, 3269

Google Scholar
23 Phillips JR. Poat JC. Slawin AMZ. Williams DJ. Wood PT. Woollins JD. J. Chem. Soc., Dalton Trans. 1995, 2369

Google Scholar
24 Poat JC. Slawin AMZ. Williams DJ. Wood PT. Woollins JD. J. Chem. Soc., Chem. Commun. 1990, 1036

Google Scholar
25 Poat JC. Slawin AMZ. Williams DJ. Wood PT. Woollins JD. Polyhedron 1992, 11: 2125

Google Scholar
26a Belton PS. Parkin IP. Williams DJ. Woollins JD. J. Chem. Soc., Chem. Commun. 1988, 1479

Google Scholar
26b Parkin IP. Williams DJ. Woollins JD. J. Chem. Soc., Chem. Commun. 1989, 58

Google Scholar
26c Parkin IP. Woollins JD.
J. Chem. Soc., Dalton Trans. 1990, 925

Google Scholar
27 Jagg PN. Kelly PF. Rzepa HS. Williams DJ. Woollins JD. Wylie W. J. Chem. Soc., Chem. Commun. 1991, 942

Google Scholar
28 Meisel M. Grunze G. Z. Anorg. Allg. Chem. 1970, 373: 265

Google Scholar
29 Slawin AMZ. Williams DJ. Wood PT. Woollins JD. J. Chem. Soc., Chem. Commun. 1987, 1741

Google Scholar
30a Kilian P. Knight FR. Woollins JD. Chem. Eur. J. 2011, 17: 2302

Google Scholar
30b Kilian P. Knight FR. Woollins JD. Coord. Chem. Rev. 2011, 255: 1387

Google Scholar
31 Kilian P. Philp D. Slawin AMZ. Woollins JD. Eur. J. Inorg. Chem. 2003, 249

Google Scholar
32 Kilian P. Slawin AMZ. Woollins JD. Chem. Eur. J. 2003, 9: 215

Google Scholar
33a Kilian P. Slawin AMZ. Woollins JD. Chem. Commun. (Cambridge) 2003, 1174

Google Scholar
33b Kilian P. Milton HL. Slawin AMZ. Woollins JD. Inorg. Chem. 2004, 43: 2252

Google Scholar
34a Kilian P. Slawin AMZ. Woollins JD. Dalton Trans. 2006, 2175

Google Scholar
34b Somisara DMUK. Bühl M. Lebl T. Richardson NV. Slawin AMZ. Woollins JD. Kilian P. Chem. Eur. J. 2010, 17: 2666

Google Scholar
35a Knight FR. Fuller AR. Bühl M. Slawin AMZ. Woollins JD. Chem. Eur. J. 2010, 16: 7503

Google Scholar
35b Knight FR. Fuller AR. Bühl M. Slawin AMZ. Woollins JD. Chem. Eur. J. 2010, 16: 7605

Google Scholar
35c Knight FR. Fuller AR. Bühl M. Slawin AMZ. Woollins JD. Chem. Eur. J. 2010, 16: 7617

Google Scholar
35d Knight FR. Fuller AR. Bühl M. Slawin AMZ. Woollins JD. Inorg. Chem. 2010, 49: 7577

Google Scholar
36a Aschenbach LK. Knight FR. Randall RAM. Cordes DB. Baggott A. Bühl M. Slawin AMZ. Woollins JD. Dalton Trans. 2012, 41: 3141

Google Scholar
36b Knight FR. Arachchige KSA. Randall RAM. Bühl M. Slawin AMZ. Woollins JD. Dalton Trans. 2012, 41: 3154

Google Scholar
37a Fitzmaurice JC. Williams DJ. Wood PT. Woollins JD. J. Chem. Soc., Chem. Commun. 1988, 741

Google Scholar
37b Wood PT. Woollins JD. J. Chem. Soc., Chem. Commun. 1988, 1190

Google Scholar
37c Wood PT. Woollins JD. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 41: 51

Google Scholar
37d Pilkington MJ. Slawin AMZ. Williams DJ. Wood PT. Woollins JD. Heteroat. Chem. 1990, 1: 351

Google Scholar
38a Karaghiosoff K. Jochem G. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 41: 460

Google Scholar
38b Karaghiosoff K. Eckstein K. Motzer R. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 93: 185

Google Scholar
38c Karaghiosoff K. Habilitation thesis University of Munich; Germany: 1997.

Google Scholar
38d Großman G. Ohms G. Kruger K. Karaghiosoff K. Eckstein K. Hahn J. Hopp A. Malkina OL. Hrobarik P. Z. Anorg. Allg. Chem. 2001, 627: 1269

Google Scholar
39 Hall SW. Pilkington MJ. Slawin AMZ. Williams DJ. Woollins JD. Polyhedron 1991, 10: 261

Google Scholar
40 Parkin IP. Pilkington MJ. Slawin AMZ. Williams DJ. Woollins JD. Polyhedron 1990, 9: 987

Google Scholar
41 Woollins JD. J. Chem. Soc., Dalton Trans. 1996, 2893

Google Scholar
42 Ly TQ. Slawin AMZ. Woollins JD. Angew. Chem., Int. Ed. 1998, 37: 2501

Google Scholar
43a Foreman MRSt. J. Slawin AMZ. Woollins JD. J. Chem. Soc., Dalton Trans. 1999, 1175

Google Scholar
43b Foreman MRSt. J. Slawin AMZ. Woollins JD. J. Chem. Soc., Dalton Trans. 1996, 3653

Google Scholar
43c Foreman MRSt. J. Slawin AMZ. Woollins JD. Chem. Commun. (Cambridge) 1997, 1269

Google Scholar
43d Foreman MRSt. J. Slawin AMZ. Woollins JD. Chem. Commun. (Cambridge) 1997, 855

Google Scholar
44 Baxter I. Hill AF. Malget JM. White AJP. Williams DJ. Chem. Commun. (Cambridge) 1997, 2049

Google Scholar
45 Gray IP. Bhattacharyya P. Slawin AMZ. Woollins JD. Chem. Eur. J. 2005, 11: 6221

Google Scholar
46 Parveen S. Kilian P. Slawin AMZ. Woollins JD. Dalton Trans. 2006, 2586

Google Scholar
47 Kilian P. Slawin AMZ. Woollins JD. Chem. Commun. (Cambridge) 2001, 2288

Google Scholar
48a Cava MP. Levinson MI. Tetrahedron 1985, 41: 5061

Google Scholar
48b Cherkasov RA. Kutyrev GA. Pudovik AN. Tetrahedron 1985, 41: 2567

Google Scholar
49a Rothenberger A. Shi W. Shafaei-Fallah M. Chem. Eur. J. 2007, 13: 5974

Google Scholar
49b Shi W. Shafaei-Fallah M. Rothenberger A. Chem. Commun. (Cambridge) 2007, 4255

Google Scholar
49c Shi W. Zhang L. Shafaei-Fallah M. Rothenberger A. Z. Anorg. Allg. Chem. 2007, 633: 440

Google Scholar
49d Shi W. Shafaei-Fallah M. Zhang L. Anson CE. Matern E. Rothenberger A. Chem. Eur. J. 2007, 13: 598

Google Scholar
50a Gray IP. Slawin AMZ. Woollins JD. Dalton Trans. 2005, 2188

Google Scholar
50b Hua G. Randall RAM. Slawin AMZ. Woollins JD. Z. Anorg. Allg. Chem. 2011, 637: 1800

Google Scholar
51 Hua G. Woollins JD. Organic Phosphorus-Selenium Chemistry, In Selenium and Tellurium Chemistry Woollins JD. Laitinen R. Springer; Berlin: 2011. Chap. 1.

Google Scholar
52 Hua G. Woollins JD. Angew. Chem. Int. Ed. 2009, 48: 1368

Google Scholar
53 Hua G. Li Y. Slawin AMZ. Woollins JD. Org. Lett. 2006, 8: 5251

Google Scholar
54 Bethke J. Karaghiosoff K. Wessjohann LA. Tetrahedron Lett. 2003, 44: 6911

Google Scholar
55 Bhattacharyya P. Woollins JD. Tetrahedron Lett. 2001, 42: 5949

Google Scholar
56 Li Y. Hua G. Slawin AMZ. Woollins JD. Molecules 2009, 14: 884

Google Scholar
57 Hua G. Li Y. Slawin AMZ. Woollins JD. Dalton Trans. 2007, 1477

Google Scholar
58 Bhattacharyya P. Slawin AMZ. Woollins JD. J. Chem. Soc., Dalton Trans. 2001, 300

Google Scholar
59 Bhattacharyya P. Slawin AMZ. Woollins JD. Chem. Eur. J. 2002, 8: 2705

Google Scholar
60 Hua G. Li Y. Slawin AMZ. Woollins JD. Chem. Commun. (Cambridge) 2007, 1465

Google Scholar
61 Bhattacharyya P. Slawin AMZ. Woollins JD. Angew. Chem. Int. Ed. 2000, 39: 1973

Google Scholar
62 Hua G. Henry JB. Li Y. Mount AR. Slawin AMZ. Woollins JD. Org. Biomol. Chem. 2010, 8: 1655

Google Scholar
63 Hua G. Li Y. Fuller AL. Slawin AMZ. Woollins JD. Eur. J. Org. Chem. 2009, 1612

Google Scholar
64a Bhattacharyya P. Slawin AMZ. Woollins JD.
J. Organomet. Chem. 2001, 623: 116

Google Scholar
64b Hua G. Fuller AL. Li Y. Slawin AMZ. Woollins JD. New J. Chem. 2010, 34: 1565

Google Scholar
65a Hua G. Li Y. Slawin AMZ. Woollins JD. Angew. Chem. Int. Ed. 2008, 47: 2857

Google Scholar
65b Hua G. Li Y. Fuller AL. Slawin AMZ. Woollins JD. Eur. J. Org. Chem. 2010, 2607

Google Scholar
65c Hua G. Li Y. Slawin AMZ. Woollins JD. Tetrahedron 2008, 64: 5442

Google Scholar
66 Hua G. Li Y. Slawin AMZ. Woollins JD. Polyhedron 2011, 30: 805

Google Scholar
67 Hua G. Fuller AL. Bühl M. Slawin AMZ. Woollins JD. Eur. J. Org. Chem. 2011, 3067

Google Scholar
68 Hua G. Griffin JM. Ashbrook SE. Slawin AMZ. Woollins JD. Angew. Chem. Int. Ed. 2011, 50: 4123

Google Scholar