Abstract
Hexadecyltributylphosphonium azide (QN3 ) is easily accessible and highly lipophilic, resulting in good solubility in nonpolar
solvents like cyclohexane. The low melting point of this reagent allows convenient
usage as a (supercooled) melt. Thus, extremely rapid nucleophilic substitution reactions
and isolation of unstable products by simple re-condensation are possible. Utilizing
these properties, the application of QN3 in the synthesis of organic azides is successful even in cases in which classical
methods have failed. This is demonstrated in this review by several examples, including
unstable starting materials and substrates with steric hindrance or i-strain, or dealing
with rapid subsequent reactions, either desired or not, of the generated azides.
1 Introduction
2 Synthesis and Properties of Hexadecyltributylphosphonium Azide (QN3 )
3 SN 2 Reactions
3.1 With Steric Hindrance
3.2 With Internal Strain
4 Other Nucleophilic Substitutions
5 Nucleophilic Substitution with Rapid Subsequent Reactions of the Azides
5.1 Rapid Sigmatropic Rearrangements
5.2 Rapid Electrocyclic Ring Opening
6 Conclusion
Key words
azides - nitrogen heterocycles - rearrangements - small-ring compounds - substitution
reactions
References
1a </A>
Bräse S.
Gil C.
Knepper K.
Zimmermann V.
Angew. Chem. Int. Ed.
2005,
44:
5188 ; Angew. Chem. 2005 , 117 , 5320
1b </A>
The Chemistry of Functional Groups Supplement D2: The Chemistry of Halides, Pseudo-Halides
and Azides
Parts 1 and 2:
Patai S.
Rappoport Z.
Wiley;
Chichester:
1995.
1c </A>
Hassner A.
In Houben-Weyl
Vol. E16a, Part 2, 4th ed.:
Klamann D.
Thieme;
Stuttgart:
1990.
p.1243
1d </A>
Scriven EFV.
Turnbull K.
Chem. Rev.
1988,
88:
297
1e </A>
Benson FR.
The High Nitrogen Compounds
Wiley;
New York:
1984.
1f </A>
Azides and Nitrenes
Scriven EFV.
Academic;
Orlando (USA):
1984.
1g </A>
The Chemistry of Functional Groups, Supplement D: The Chemistry of Halides, Pseudo-Halides
and Azides
Patai S.
Rappoport Z.
Wiley;
Chichester:
1983.
1h </A>
The Chemistry of the Azido Group
Patai S.
Wiley;
London:
1971.
<A NAME="RE18307SS-2">2 </A>
Abramovitch RA.
Kyba EP. In
The Chemistry of the Azido Group
Patai S.
Wiley;
London:
1971.
p.221
3a </A>
Schmidt KF.
Angew. Chem.
1923,
36:
511
3b </A>
Schmidt KF.
Ber. Dtsch. Chem. Ges.
1924,
57:
704
3c </A>
Krow GR.
Tetrahedron
1981,
37:
1283
3d </A>
Pearson WH.
Hutta DA.
Fang W.
J. Org. Chem.
2000,
65:
8326
3e </A>
Pearson WH.
Fang W.
J. Org. Chem.
2000,
65:
7158
<A NAME="RE18307SS-4">4 </A>
Engel A. In
Houben-Weyl
Klamann D.
Thieme;
Stuttgart:
1990.
<A NAME="RE18307SS-5">5 </A>
Sheradsky T. In
The Chemistry of the Azido Group
Patai S.
Wiley;
London:
1971.
p.331
6a </A>
Staudinger H.
Meyer J.
Helv. Chim. Acta
1919,
2:
635
6b </A>
Gololobov YG.
Zhmurova IN.
Kasukhin LF.
Tetrahedron
1981,
37:
437
6c </A>
Gololobov YG.
Kasukhin LF.
Tetrahedron
1992,
48:
1353
7a </A>
Huisgen R.
Angew. Chem., Int. Ed. Engl.
1963,
2:
565 ; Angew. Chem. 1963 , 75 , 604
7b </A>
Huisgen R. In
1,3-Dipolar Cycloaddition Chemistry
Vol. 1:
Padwa A.
Wiley;
New York:
1984.
p.1
8a </A>
Rostovtsev VV.
Green LG.
Fokin VV.
Sharpless KB.
Angew. Chem. Int. Ed.
2002,
41:
2596 ; Angew. Chem. 2002 , 114 , 2708
8b </A>
Tornøe CW.
Christensen C.
Meldal M.
J. Org. Chem.
2002,
67:
3057
9a </A>
Bock VD.
Hiemstra H.
van Maarseveen JH.
Eur. J. Org. Chem.
2006,
51
9b </A>
Lutz J.-F.
Angew. Chem. Int. Ed.
2007,
46:
1018 ; Angew. Chem. 2007 , 119 , 1036
<A NAME="RE18307SS-10">10 </A>
Hemmer R.
Lürken W. In
Houben-Weyl
Vol. E16d, Part 2, 4th ed.:
Klamann D.
Thieme;
Stuttgart:
1992.
p.646
<A NAME="RE18307SS-11">11 </A>
Ferrier R.
J. Carbohydr. Chem.
2003,
34:
136
<A NAME="RE18307SS-12">12 </A>
Breslow DS.
In Azides and Nitrenes
Scriven EFV.
Academic;
Orlando (USA):
1984.
p.491
13a </A>
Hammerl A.
Klapötke TM.
Rocha R.
Eur. J. Inorg. Chem.
2006,
2210
13b </A>
Dabbagh HA.
Lwowski W.
J. Org. Chem.
2000,
65:
7284
13c </A>
Kurz D.
Reinhold J.
J. Mol. Struct. (Theochem)
1999,
492:
187
13d </A>
Cubero E.
Orozco M.
Luque FJ.
J. Org. Chem.
1998,
63:
2354
13e </A>
Henry RA.
Finnegan WG.
Lieber E.
J. Am. Chem. Soc.
1954,
76:
88
<A NAME="RE18307SS-14">14 </A>
Gagneux A.
Winstein S.
Young WG.
J. Am. Chem. Soc.
1960,
82:
3766
15a </A>
L’abbé G.
Hassner A.
Angew. Chem., Int. Ed. Engl.
1971,
10:
98 ; Angew. Chem. 1971 , 83 , 103
15b </A>
Smolinsky G.
Pryde CA. In
The Chemistry of the Azido Group
Patai S.
Wiley;
London:
1971.
p.555
15c </A>
Hassner A. In Azides and Nitrenes
Scriven EFV.
Academic;
Orlando (USA):
1984.
p.35
15d </A>
Banert K. In
Houben-Weyl
Vol. E15, 4th ed.:
Kropf H.
Schaumann E.
Thieme;
Stuttgart:
1993.
<A NAME="RE18307SS-16">16 </A>
Lwowski W. In
The Chemistry of the Azido Group
Patai S.
Wiley;
London:
1971.
p.503
17a </A>
Nair V. In
The Chemistry of Heterocyclic Compounds, Small-Ring Heterocycles
Vol. 42, Part 1:
Hassner A.
Wiley;
New York:
1983.
p.215
17b </A>
Backes J. In
Houben-Weyl
Vol. E16c, 4th ed.:
Klamann D.
Thieme;
Stuttgart:
1992.
p.317
<A NAME="RE18307SS-18">18 </A>
Ohta S.
Tsuno N.
Nakamura S.
Taguchi N.
Yamashita M.
Kawasaki I.
Fujieda M.
Heterocycles
2000,
53:
1939
19a </A>
Evans DA.
Britton TC.
Ellman JA.
Dorow RL.
J. Am. Chem. Soc.
1990,
112:
4011
19b </A>
Derrer S.
Davies JE.
Holmes AB.
J. Chem. Soc., Perkin Trans. 1
2000,
2943
19c </A>
Derrer S.
Davies JE.
Holmes AB.
J. Chem. Soc., Perkin Trans. 1
2000,
2957
<A NAME="RE18307SS-20">20 </A>
Smith PAS. In
Azides and Nitrenes
Scriven EFV.
Academic;
Orlando (USA):
1984.
p.95
<A NAME="RE18307SS-21">21 </A>
Griess P.
Proc. R. Soc. London
1864,
13:
375
22a </A>
Anselme J.-P.
Fischer W.
Tetrahedron
1969,
25:
855
22b </A>
Reed JO.
Lwowski W.
J. Org. Chem.
1971,
36:
2864
23a </A>
Nyffeler PT.
Liang C.-H.
Koeller KM.
Wong C.-H.
J. Am. Chem. Soc.
2002,
124:
10773
23b </A>
Liu Q.
Tor Y.
Org. Lett.
2003,
5:
2571
23c </A>
Yan R.-B.
Yang F.
Wu Y.
Zhang L.-H.
Ye X.-S.
Tetrahedron Lett.
2005,
46:
8993
23d </A>
Beckmann HSG.
Wittmann V.
Org. Lett.
2007,
9:
1
24a </A>
Kirschning A.
Monenschein H.
Schmeck C.
Angew. Chem. Int. Ed.
1999,
38:
2594 ; Angew. Chem. 1999 , 111 , 272
24b </A>
Kirschning A.
Jesberger M.
Monenschein H.
Tetrahedron Lett.
1999,
40:
8999
24c </A>
Kirschning A.
Hashem MA.
Monenschein H.
Rose L.
Schöning K.-U.
J. Org. Chem.
1999,
64:
6522
<A NAME="RE18307SS-25">25 </A>
Hassner A.
Acc. Chem. Res.
1971,
4:
9
<A NAME="RE18307SS-26">26 </A>
Banert K.
Lehmann J.
In Modern Allene Chemistry
Krause N.
Hashmi ASK.
Wiley-VCH;
Weinheim:
2004.
p.359
27a </A>
Myers JK.
Jacobsen EN.
J. Am. Chem. Soc.
1999,
121:
8959
27b </A>
Horstmann TE.
Guerin DJ.
Miller SJ.
Angew. Chem. Int. Ed.
2000,
39:
3635 ; Angew. Chem. 2000 , 112 , 3781
<A NAME="RE18307SS-28">28 </A>
Nishiyama K.
Oba M.
Watanabe A.
Tetrahedron
1987,
43:
693
29a </A>
Chavan SP.
Subbarao YT.
Tetrahedron Lett.
1999,
40:
5073
29b </A>
Seeberger PH.
Roehrig S.
Schell P.
Wang Y.
Christ WJ.
Carbohydr. Res.
2000,
328:
61
29c </A>
Nair V.
George TG.
Sheeba V.
Augustine A.
Balagopal L.
Nair LG.
Synlett
2000,
1597
29d </A>
Nair V.
Nair LG.
George TG.
Augustine A.
Tetrahedron
2000,
56:
7607
29e </A>
Griesbeck AG.
Lex J.
Saygin KM.
Steinwascher J.
Chem. Commun.
2000,
2205
29f </A>
Curini M.
Epifano F.
Marcotullio MC.
Rosati O.
Tetrahedron Lett.
2002,
43:
1201
30a </A>
Evans DA.
Ellman JA.
Dorow RL.
Tetrahedron Lett.
1987,
28:
1123
30b </A>
Enders D.
Klein D.
Synlett
1999,
719
<A NAME="RE18307SS-31">31 </A>
Grundmann C. In
Houben-Weyl
Vol. 10/3, 4th ed.:
Stroh R.
Thieme;
Stuttgart:
1965.
p.777
<A NAME="RE18307SS-32">32 </A>
Alvarez SC.
Alvarez MT.
Synthesis
1997,
413
<A NAME="RE18307SS-33">33 </A> Review:
Narayan S.
Fokin VV.
Sharpless KB. In Organic Reactions in Water
Lindström UM.
Blackwell Publishers;
Oxford:
2007.
p.350
34a </A>
Lowry TH.
Richardson KS.
Mechanismen und Theorie in der Organischen Chemie
Verlag Chemie;
Weinheim:
1980.
Chap. 4.
34b </A>
Harris JM.
Raber DJ.
Hall RE.
Schleyer P.
J. Am. Chem. Soc.
1970,
92:
5729
35a </A>
Landini D.
Maia A.
Montanari F.
J. Am. Chem. Soc.
1978,
100:
2796
35b </A>
Landini D.
Maia A.
Montanari F.
Nouv. J. Chim.
1979,
3:
575
35c </A>
Maia A.
Pure Appl. Chem.
1995,
67:
697
36a </A>
Landini D.
Maia A.
Montanari F.
Rolla F.
J. Org. Chem.
1983,
48:
3774
36b </A>
Ando T.
Kimura T.
Yamataka H.
Adv. Chem. Ser.
1987,
215:
103
<A NAME="RE18307SS-37">37 </A>
Banert K.
Kirmse W.
J. Am. Chem. Soc.
1982,
104:
3766
<A NAME="RE18307SS-38">38 </A>
Ohtani N.
Murakawa S.
Watanabe K.
Tsuchimoto D.
Sato D.
J. Chem. Soc., Perkin Trans. 2
2000,
1851
39a </A>
Landini D.
Maia A.
Montanari F.
J. Chem. Soc., Perkin Trans. 2
1983,
461
39b </A>
De Giorgi M.
Landini D.
Maia A.
Penso M.
Synth. Commun.
1987,
17:
521
<A NAME="RE18307SS-40">40 </A>
Banert K.
Chem. Ber.
1985,
118:
1564
<A NAME="RE18307SS-41">41 </A>
Banert K.
Lehmann J.
Quast H.
Meichsner G.
Regnat D.
Seiferling B.
J. Chem. Soc., Perkin Trans. 2
2002,
126
<A NAME="RE18307SS-42">42 </A>
Banert K.
Joo Y.-H.
Rüffer T.
Walfort B.
Lang H.
Angew. Chem. Int. Ed.
2007,
46:
1168 ; Angew. Chem. 2007 , 119 , 1187
<A NAME="RE18307SS-43">43 </A>
Banert, K.; Joo, Y.-H. unpublished results.
<A NAME="RE18307SS-44">44 </A>
Brückner R.
Reaktionsmechanismen
Elsevier Spektrum;
Heidelberg:
2004.
p.70
45a </A>
Brown HC.
Krishnamurthy S.
J. Am. Chem. Soc.
1973,
95:
1669
45b </A>
Roberts JD.
Chambers VC.
J. Am. Chem. Soc.
1951,
73:
5034
45c </A>
Streitwieser A.
Chem. Rev.
1956,
56:
571
45d </A>
Elias H.
Krutzik S.
Chem. Ber.
1966,
99:
1026
45e </A>
Gounelle Y.
Solgadi D.
Bull. Soc. Chim. Fr.
1973,
3019
45f </A>
Chang W.-S.
Elias H.
Chem. Ber.
1970,
103:
842
46a </A>
Cristol SJ.
Brindell GD.
J. Am. Chem. Soc.
1954,
76:
5699
46b </A>
Nickon A.
Hammons JH.
J. Am. Chem. Soc.
1964,
86:
3322
46c </A>
Schaefer JP.
Weinberg DS.
J. Org. Chem.
1965,
30:
2635
46d </A>
Schaefer JP.
Weinberg DS.
J. Org. Chem.
1965,
30:
2639
46e </A>
Tanigawa Y.
Kanamaru H.
Murahashi S.-I.
Tetrahedron Lett.
1975,
4655
46f </A>
Brown HC.
Krishnamurthy S.
Tetrahedron
1979,
35:
567
46g </A>
Fischer W.
Grob CA.
von Sprecher G.
Helv. Chim. Acta
1980,
63:
806
47a </A>
Grob CA.
Lutz E.
Helv. Chim. Acta
1981,
64:
153
47b </A>
Brown HC.
The Nonclassical Ion Problem
Plenum;
New York:
1977.
Chap. 8.
47c </A>
Takeuchi K.
Kato Y.
Moriyama T.
Okamoto K.
Chem. Lett.
1981,
935
48a </A>
Roberts DD.
Hendrickson W.
J. Org. Chem.
1969,
34:
2415
48b </A>
Nordlander JE.
Gruetzmacher RR.
Kelly WJ.
Jindal SP.
J. Am. Chem. Soc.
1974,
96:
181
<A NAME="RE18307SS-49">49 </A> A critical view on nucleophilic solvent participation in solvolysis:
Gajewski JJ.
J. Am. Chem. Soc.
2001,
123:
10877
50a </A>
Fry JL.
Lancelot CJ.
Lam LKM.
Harris JM.
Bingham RC.
Raber DJ.
Hall RE.
Schleyer P.
J. Am. Chem. Soc.
1970,
92:
2538
50b </A>
Kevill DN.
Shen BW.
J. Am. Chem. Soc.
1981,
103:
4515
<A NAME="RE18307SS-51">51 </A> Nucleophilic substitution with partial inversion was obtained in the case of
4-bromoadamantan-2-ones:
Snatzke G.
Eckhardt G.
Chem. Ber.
1968,
101:
2010
<A NAME="RE18307SS-52">52 </A>
Banert K.
Kurnianto A.
Chem. Ber.
1986,
119:
3826
53a </A>
Bone JA.
Whiting MC.
Chem. Commun.
1970,
115
53b </A>
Lenoir D.
Mison P.
Hyson E.
Schleyer P.
Saunders M.
Vogel P.
Telkowski LA.
J. Am. Chem. Soc.
1974,
96:
2157
53c </A>
Bone JA.
Pritt JR.
Whiting MC.
J. Chem. Soc., Perkin Trans. 2
1975,
1447
53d </A>
Nordlander JE.
Haky JE.
J. Am. Chem. Soc.
1981,
103:
1518
53e </A>
Cheung CK.
Tseng LT.
Lin M.-H.
Srivastava S.
le Noble WJ.
J. Am. Chem. Soc.
1986,
108:
1598
53f </A>
Lenoir D.
Chem. Ber.
1973,
106:
2366
53g </A>
Lenoir D.
Hall RE.
Schleyer P.
J. Am. Chem. Soc.
1974,
96:
2138
53h </A>
Lenoir D.
Raber DJ.
Schleyer P.
J. Am. Chem. Soc.
1974,
96:
2149
53i </A>
Kovačević D.
Goričnik B.
Majerski Z.
J. Org. Chem.
1978,
43:
4008
53j </A>
Brown HC.
The Nonclassical Ion Problem
Plenum;
New York:
1977.
p.281
<A NAME="RE18307SS-54">54 </A>
Faulkner D.
McKervey MA.
Lenoir D.
Senkler CA.
Schleyer P.
Tetrahedron Lett.
1973,
705
<A NAME="RE18307SS-55">55 </A>
Kirmse W.
Streu J.
J. Org. Chem.
1985,
50:
4187
<A NAME="RE18307SS-56">56 </A>
Kirmse W.
Kampmann K.-H.
Zellmer V.
Chem. Ber.
1987,
120:
1301
57a </A>
Gillespie P.
Ugi I.
Angew. Chem., Int. Ed. Engl.
1971,
10:
503 ; Angew. Chem. 1971 , 83 , 493
57b </A>
Stohrer W.-D.
Schmieder KR.
Chem. Ber.
1976,
109:
285
58a </A>
Woodward RB.
Hoffmann R.
J. Am. Chem. Soc.
1965,
87:
395
58b </A>
Schöllkopf U.
Angew. Chem., Int. Ed. Engl.
1968,
7:
588 ; Angew. Chem. 1968 , 80 , 603
58c </A>
Schleyer P.
Sliwinski WF.
Van Dine GW.
Schöllkopf U.
Paust J.
Fellenberger K.
J. Am. Chem. Soc.
1972,
94:
125
<A NAME="RE18307SS-59">59 </A>
Banert K.
Tetrahedron Lett.
1985,
26:
5261
60a </A>
Nicolaides A.
Nakayama T.
Yamazaki K.
Tomioko H.
Koseki S.
Stracener LL.
McMahon RJ.
J. Am. Chem. Soc.
1999,
121:
10563
60b </A>
Banert K.
Angew. Chem., Int. Ed. Engl.
1987,
26:
879 ; Angew. Chem. 1987 , 99 , 932
60c </A>
Banert K.
Chem. Ber.
1989,
122:
123
60d </A>
Pearce DS.
Lee M.-S.
Moore HW.
J. Org. Chem.
1974,
39:
1362
60e </A>
Pearce DS.
Locke MJ.
Moore HW.
J. Am. Chem. Soc.
1975,
97:
6181
60f </A>
VanAllan JA.
Priest WJ.
Marshall AS.
Reynolds GA.
J. Org. Chem.
1968,
33:
1100
60g </A>
Hall JH.
J. Am. Chem. Soc.
1965,
87:
1147
60h </A>
Hall JH.
Patterson E.
J. Am. Chem. Soc.
1967,
89:
5856
60i </A>
Smolinsky G.
Pryde CA.
J. Org. Chem.
1968,
33:
2411
<A NAME="RE18307SS-61">61 </A> Review:
Banert K.
In Houben-Weyl
Vol. E15, 4th ed.:
Kropf H.
Schaumann E.
Thieme;
Stuttgart:
1993.
p.1344
<A NAME="RE18307SS-62">62 </A>
Hassner A.
Isbister RJ.
Friederang A.
Tetrahedron Lett.
1969,
2939
<A NAME="RE18307SS-63">63 </A>
Fotsing JR.
Hagedorn M.
Banert K.
Tetrahedron
2005,
61:
8904
<A NAME="RE18307SS-64">64 </A>
Banert, K.; Hagedorn, M. unpublished results.
65a </A>
Judge RH.
Moule DC.
Biernacki A.
Benkel M.
Ross JM.
Rustenburg J.
J. Mol. Spectrosc.
1986,
116:
364
65b </A>
Clouthier DJ.
Moule DC.
J. Am. Chem. Soc.
1987,
109:
6259
65c </A>
Bogey M.
Destombes JL.
Vallee Y.
Ripoll JL.
Chem. Phys. Lett.
1988,
146:
227
65d </A>
Vallée Y.
Ripoll J.-L.
Lacombe S.
Pfister-Guillouzo G.
J. Chem. Res., Synop.
1990,
40 ; J. Chem. Res., Miniprint
1990 , 401
65e </A>
Karolczak J.
Clouthier DJ.
Judge RH.
Moule DC.
J. Mol. Spectrosc.
1991,
147:
61
65f </A>
Clouthier DJ.
Karolczak J.
Rae J.
Chan W.-T.
Goddard JD.
Judge RH.
J. Chem. Phys.
1992,
97:
1638
65g </A>
Lewis-Bevan W.
Gaston RD.
Tyrrell J.
Stork WD.
Salmon GL.
J. Am. Chem. Soc.
1992,
114:
1933
65h </A>
Bogey M.
Demuynck C.
Destombes JL.
Vallee Y.
Ripoll JL.
J. Mol. Spectrosc.
1995,
172:
344
65i </A>
Born M.
Ingemann S.
Nibbering NMM.
J. Phys. Chem.
1996,
100:
17662
65j </A>
Tyndall GS.
Orlando JJ.
Wallington TJ.
Hurley MD.
J. Phys. Chem. A
2001,
105:
5380
66 </A>
These experiments were performed in collaboration with Dr. Hans Peter Reisenauer and
Prof. Günther Maier at the Justus-Liebig-Universität Gießen.
<A NAME="RE18307SS-67">67 </A>
Banert K.
Chem. Ber.
1989,
122:
1175
<A NAME="RE18307SS-68">68 </A>
Banert K.
Chem. Ber.
1989,
122:
1963
<A NAME="RE18307SS-69">69 </A>
Banert K.
Umlagerungen organischer Azide. Reaktionsmechanismen und Anwendungen in der Synthese
Schäuble Verlag;
Rheinfelden:
1993.
70a </A>
Huestis LD.
Andrews LJ.
J. Am. Chem. Soc.
1961,
83:
1963
70b </A>
White WN.
Norcross BE.
J. Am. Chem. Soc.
1961,
83:
1968
<A NAME="RE18307SS-71">71 </A>
Banert K.
Angew. Chem., Int. Ed. Engl.
1985,
24:
216 ; Angew. Chem. 1985 , 97, 231
<A NAME="RE18307SS-72">72 </A>
Banert, K.; Kuhtz, A. unpublished results.
73a </A>
L’abbé G.
Mahy M.
Bollyn M.
Germain G.
Scheefer G.
Bull. Soc. Chim. Belg.
1983,
92:
881
73b </A>
L’abbé G.
Bull. Soc. Chim. Belg.
1984,
93:
579
73c </A>
Hassner A.
Keogh J.
J. Org. Chem.
1986,
51:
2767
<A NAME="RE18307SS-74">74 </A>
Shiner VJ.
Humphrey JS.
J. Am. Chem. Soc.
1967,
89:
622
<A NAME="RE18307SS-75">75 </A>
Banert K.
Chem. Ber.
1989,
122:
911
<A NAME="RE18307SS-76">76 </A>
Baldwin MG.
Johnson KE.
Lovinger JA.
Parker CO.
J. Polym. Sci., Part B
1967,
5:
803
<A NAME="RE18307SS-77">77 </A>
Banert K.
Hagedorn M.
Angew. Chem., Int. Ed. Engl.
1989,
28:
1675 ; Angew. Chem. 1989 , 101 , 1710
78a </A>
Banert K.
Hagedorn M.
Angew. Chem., Int. Ed. Engl.
1990,
29:
103 ; Angew. Chem. 1990 , 102 , 90
78b </A>
Banert K.
Hagedorn M.
Knözinger E.
Becker A.
Würthwein E.-U.
J. Am. Chem. Soc.
1994,
116:
60
79a </A>
Krivopalov VP.
Shkurko OP.
Russ. Chem. Rev.
2005,
74:
339
79b </A>
Dehne H. In
Houben-Weyl
Vol. E8d, 4th ed.:
Schaumann E.
Thieme;
Stuttgart:
1994.
p.305
79c </A>
Tomé AC. In
Science of Synthesis
Vol. 13, 5th ed.:
Storr RC.
Gilchrist TL.
Thieme;
Stuttgart:
2004.
p.415
80a </A>
Banert K.
Liebigs Ann./Recl.
1997,
2005
80b </A>
Banert K.
Targets in Heterocyclic Systems
2000,
3:
1
81a </A>
Harrison T.
Owens AP.
Williams BJ.
Swain CJ.
Williams A.
Carlson EJ.
Rycroft W.
Tattersall FD.
Cascieri MA.
Chicchi GG.
Sadowski S.
Rupniak NMJ.
Hargreaves RJ.
J. Med. Chem.
2001,
44:
4296
81b </A>
Owens AP. inventors; (Merck Sharp and Dohme Ltd) WO 9629317.
; Chem. Abstr.
1997 , 126 : 8122
81c </A>
Baker R,
Elliot J,
Stevenson GI, and
Swain CJ. inventors; (Merck Sharp & Dohme Ltd) WO 9701553.
; Chem. Abstr.
1997 , 126 : 171610
81d </A>
Baker R,
Elliot J,
Stevenson GI, and
Swain CJ. inventors; (Merck Sharp & Dohme Ltd) WO 9701554.
; Chem. Abstr.
1997 , 126 : 171611
81e </A>
Moseley JD,
Swain CJ, and
Williams BJ. inventors; (Merck Sharp & Dohme Ltd) GB 2302689.
; Chem. Abstr.
1997 , 126 : 277501
<A NAME="RE18307SS-82">82 </A>
Loren JC.
Sharpless KB.
Synthesis
2005,
1514
<A NAME="RE18307SS-83">83 </A>
Fotsing JR.
Banert K.
Eur. J. Org. Chem.
2005,
3704
<A NAME="RE18307SS-84">84 </A>
Priebe H.
Angew. Chem., Int. Ed. Engl.
1984,
23:
736 ; Angew. Chem. 1984 , 96 , 728
<A NAME="RE18307SS-85">85 </A>
Banert K.
Chem. Ber.
1987,
120:
1891
86a </A>
Padwa A.
Goldstein SI.
Rosenthal RJ.
J. Org. Chem.
1987,
52:
3278
86b </A>
Bickelhaupt F.
de Wolf WH.
Recl. Trav. Chim. Pays-Bas
1988,
107:
459
87a </A>
Padwa A.
Blacklock TJ.
Carlsen PHJ.
Pulwer M.
J. Org. Chem.
1979,
44:
3281
87b </A>
Padwa A.
Smolanow J.
Tremper A.
J. Org. Chem.
1976,
41:
543
<A NAME="RE18307SS-88">88 </A>
Gallagher TC.
Storr RC.
Tetrahedron Lett.
1981,
22:
2905
<A NAME="RE18307SS-89">89 </A>
Hassner A.
Keogh J.
Tetrahedron Lett.
1975,
1575
90a </A>
Banert K.
Köhler F.
Angew. Chem. Int. Ed.
2001,
40:
174 ; Angew. Chem. 2001 , 113 , 173
90b </A>
Banert K.
Grimme S.
Herges R.
Heß K.
Köhler F.
Mück-Lichtenfeld C.
Würthwein E.-U.
Chem. Eur. J.
2006,
12:
7467
<A NAME="RE18307SS-91">91 </A>
Kirmse W.
Rondan NG.
Houk KN.
J. Am. Chem. Soc.
1984,
106:
7989
<A NAME="RE18307SS-92">92 </A>
Banert K.
Hagedorn M.
Müller A.
Eur. J. Org. Chem.
2001,
1089
