References
Recent reviews:
<A NAME="RM03803SS-1A">1a</A>
Tavener SJ.
Clark JH.
J. Fluorine Chem.
2003,
123:
31
<A NAME="RM03803SS-1B">1b</A>
Zhang W.
Tetrahedron
2003,
59:
4475
<A NAME="RM03803SS-1C">1c</A>
Pozzi G.
Shepperson I.
Coord. Chem. Rev.
2003,
242:
115
<A NAME="RM03803SS-1D">1d</A>
Yoshida J.
Itami K.
Chem. Rev.
2002,
102:
3693
<A NAME="RM03803SS-1E">1e</A>
Dobbs AP.
Kimberley MR.
J. Fluorine Chem.
2002,
118:
3
<A NAME="RM03803SS-1F">1f</A>
Curran DP.
Pure Appl. Chem.
2000,
72:
1649
<A NAME="RM03803SS-1G">1g</A>
Curran DP. In Stimulating Concepts in Chemistry
Stoddard F.
Reinhoudt D.
Shibasaki M.
Wiley-VCH;
New York:
2000.
p.25-37
<A NAME="RM03803SS-1H">1h</A>
de Wolf E.
van Koten G.
Deelman B.-J.
Chem. Soc. Rev.
1999,
28:
37
<A NAME="RM03803SS-1I">1i</A>
Barthel-Rosa LP.
Gladysz JA.
Coord. Chem. Rev.
1999,
190-192:
587
<A NAME="RM03803SS-1J">1j</A>
Betzemeier B.
Knochel P.
Top. Curr. Chem.
1999,
206:
61
<A NAME="RM03803SS-1K">1k</A>
Fish RH.
Chem. Eur. J.
1999,
5:
1677
<A NAME="RM03803SS-1L">1l</A>
Cavazzini M.
Montanari F.
Pozzi G.
Quici S.
J. Fluorine Chem.
1999,
94:
183
<A NAME="RM03803SS-1M">1m</A>
Curran DP.
Angew. Chem. Int. Ed.
1998,
37:
1174
<A NAME="RM03803SS-1N">1n</A>
Horváth IT.
Acc. Chem. Res.
1998,
31:
641
<A NAME="RM03803SS-1O">1o</A>
A collection of articles can be found in a special issue on Fluorous Chemistry, Tetrahedron Gladysz, J. A.; Curran, D. P., Eds. 2002, 58, 3823-4131.
<A NAME="RM03803SS-2">2</A> A valuable reference will be available soon:
Handbook of Fluorous Chemistry
Gladysz JA.
Curran DP.
Horváth IT.
Wiley-VCH;
Weinheim:
2004.
p.in press
<A NAME="RM03803SS-3A">3a</A>
Cavazzini M.
Quici S.
Pozzi G.
Tetrahedron
2002,
58:
3943
<A NAME="RM03803SS-3B">3b</A>
Curran DP.
Synlett
2001,
1488
<A NAME="RM03803SS-3C">3c</A>
Curran DP.
Luo Z.
J. Am. Chem. Soc.
1999,
121:
9069
<A NAME="RM03803SS-3D">3d</A>
Kainz S.
Luo Z.
Curran DP.
Leitner W.
Synthesis
1998,
1425
<A NAME="RM03803SS-4A">4a</A>
Nakamura H.
Usui T.
Kuroda H.
Ryu I.
Matsubara H.
Yasuda S.
Curran DP.
Org. Lett.
2003,
5:
1167
<A NAME="RM03803SS-4B">4b</A>
Ryu I.
Matsubara H.
Yasuda S.
Nakamura H.
Curran DP.
J. Am. Chem. Soc.
2002,
124:
12946
<A NAME="RM03803SS-4C">4c</A>
Luo Z.
Swaleh SM.
Theil F.
Curran DP.
Org. Lett.
2002,
4:
2585
<A NAME="RM03803SS-4D">4d</A>
Nakamura H.
Linclau B.
Curran DP.
J. Am. Chem. Soc.
2001,
123:
10119
<A NAME="RM03803SS-5">5</A>
Isihara K.
Kondo S.
Yamamoto H.
Synlett
2001,
1371
<A NAME="RM03803SS-6A">6a</A>
Wende M.
Gladysz JA.
J. Am. Chem. Soc.
2003,
125:
5861
<A NAME="RM03803SS-6B">6b</A>
Wende M.
Meier R.
Gladysz JA.
J. Am. Chem. Soc.
2001,
123:
11490
<A NAME="RM03803SS-7A">7a</A>
Dandapani S.
Curran DP.
Tetrahedron
2002,
58:
3855
<A NAME="RM03803SS-7B">7b</A>
Dobbs AP.
McGregor-Johnson C.
Tetrahedron Lett.
2002,
43:
2807
<A NAME="RM03803SS-7C">7c</A>
Rábai J.
Szabó D.
Borbás EK.
Kövesi I.
Kövesdi I.
Csámpai A.
Gömöry Á.
Pashinnik VE.
Shermolovich YG.
J. Fluorine Chem.
2002,
114:
199
<A NAME="RM03803SS-8">8</A> Our work:
Markowicz MW.
Dembinski R.
Org. Lett.
2002,
4:
3785
<A NAME="RM03803SS-9">9</A>
Crich D.
Neelamkavil S.
J. Am. Chem. Soc.
2001,
123:
7449
<A NAME="RM03803SS-10">10</A>
Hao X.
Yamazaki O.
Yoshida A.
Nishikido J.
Tetrahedron Lett.
2003,
44:
4977
<A NAME="RM03803SS-11">11</A>
Barrett AGM.
Braddock DC.
Catterick D.
Chadwick D.
Henschke JP.
McKinnell RM.
Synlett
2000,
847
<A NAME="RM03803SS-12A">12a</A>
Vallin KSA.
Zhang Q.
Larhed M.
Curran DP.
Hallberg A.
J. Org. Chem.
2003,
68:
6639
<A NAME="RM03803SS-12B">12b</A>
Moineau J.
Pozzi G.
Quici S.
Sinou D.
Tetrahedron Lett.
1999,
40:
7683
<A NAME="RM03803SS-13">13</A>
Tzschucke CC.
Markert C.
Glatz H.
Bannwarth W.
Angew. Chem. Int. Ed.
2002,
41:
4500
<A NAME="RM03803SS-14">14</A>
Markert C.
Bannwarth W.
Helv. Chim. Acta
2002,
85:
1877
<A NAME="RM03803SS-15A">15a</A>
Hoshino M.
Degenkolb P.
Curran DP.
J. Org. Chem.
1997,
62:
8341
<A NAME="RM03803SS-15B">15b</A>
Curran DP.
Hoshino M.
J. Org. Chem.
1996,
61:
6480
<A NAME="RM03803SS-16">16</A>
Chen D.
Qing F.
Huang Y.
Org. Lett.
2002,
4:
1003
Selected recent papers/reviews:
<A NAME="RM03803SS-17A">17a</A>
Shangguan N.
Katukojvala S.
Greenberg R.
Williams LJ.
J. Am. Chem. Soc.
2003,
125:
7754
<A NAME="RM03803SS-17B">17b</A>
Carpino LA.
Ghassemi S.
Ionescu D.
Ismail M.
Sadat-Aalaee D.
Truran GA.
Mansour EME.
Siwruk GA.
Eynon JS.
Morgan B.
Org. Process Res. Dev.
2003,
7:
28
<A NAME="RM03803SS-17C">17c</A>
Albericio F.
Chinchilla R.
Dodsworth DJ.
Najera C.
Org. Prep. Proced. Int.
2001,
33:
205
<A NAME="RM03803SS-18">18</A>
Luo Z.
Williams J.
Read RW.
Curran DP.
J. Org. Chem.
2001,
66:
4261
<A NAME="RM03803SS-19A">19a</A>
Filippov DV.
van Zoelen DJ.
Oldfield SP.
van der Marel GA.
Overkleeft HS.
Drijfhout JW.
van Boom JH.
Tetrahedron Lett.
2002,
43:
7809
<A NAME="RM03803SS-19B">19b</A>
Curran DP.
Amatore M.
Guthrie D.
Campbell M.
Go E.
Luo Z.
J. Org. Chem.
2003,
68:
4643
Recent representative examples of applications of chloro-1,3,5-triazine:
<A NAME="RM03803SS-20A">20a</A>
De Luca L.
Giacomelli G.
Porcheddu A.
Org. Lett.
2002,
4:
553
<A NAME="RM03803SS-20B">20b</A>
De Luca L.
Giacomelli G.
Porcheddu A.
Org. Lett.
2001,
3:
3041
<A NAME="RM03803SS-20C">20c</A>
Rayle HL.
Fellmeth L.
Org. Process Res. Dev.
1999,
3:
172
<A NAME="RM03803SS-20D">20d</A>
Lee PH.
Sawan SP.
Modrusan Z.
Arnold LJ.
Reynolds MA.
Bioconjugate Chem.
2002,
13:
97
<A NAME="RM03803SS-20E">20e</A> For polystyrene-supported chlorotriazine couplings, see:
Bork JT.
Lee JW.
Chang Y.-T.
Tetrahedron Lett.
2003,
44:
6141
<A NAME="RM03803SS-20F">20f</A> See also:
Masala S.
Taddei M.
Org. Lett.
1999,
1:
1355
<A NAME="RM03803SS-21A">21a</A>
Giacomelli G.
Porcheddu A.
Salaris M.
Org. Lett.
2003,
5:
2715
<A NAME="RM03803SS-21B">21b</A>
De Luca L.
Giacomelli G.
Porcheddu A.
J. Org. Chem.
2002,
67:
6272
<A NAME="RM03803SS-22A">22a</A>
Carpino LA.
Beyermann M.
Wenschuh H.
Bienert M.
Acc. Chem. Res.
1996,
29:
268
<A NAME="RM03803SS-22B">22b</A>
Carpino LA.
Mansour EME.
Sadat-Aalaee D.
J. Org. Chem.
1991,
56:
2611
<A NAME="RM03803SS-22C">22c</A>
Carpino LA.
Sadat-Aalaee D.
Chao HG.
DeSelms RH.
J. Am. Chem. Soc.
1990,
112:
9651
<A NAME="RM03803SS-23">23</A>
Carpino LA.
Ionescu D.
El-Faham A.
Beyermann M.
Henklein P.
Hanay C.
Wenschuh H.
Bienert M.
Org. Lett.
2003,
5:
975
<A NAME="RM03803SS-24">24</A>
Kami
ñski ZJ.
Biopolymers
2000,
55:
140
<A NAME="RM03803SS-25A">25a</A>
Cronin JS.
Ginah FO.
Murray AR.
Copp JD.
Synth. Commun.
1996,
26:
3491
<A NAME="RM03803SS-25B">25b</A>
Weber AJM.
Huysmans WGB.
Mijs WJ.
Bovée WMMJ.
Smidt J.
Vriend J.
Recl. Trav. Chim. Pays-Bas
1978,
97:
107
<A NAME="RM03803SS-25C">25c</A>
Dudley JR.
Thurston JT.
Schaefer FC.
Holm-Hansen D.
Hull CJ.
Adams P.
J. Am. Chem. Soc.
1951,
73:
2986
<A NAME="RM03803SS-26A">26a</A>
Bandgar BP.
Pandit SS.
Tetrahedron Lett.
2003,
44:
3855
<A NAME="RM03803SS-26B">26b</A>
Bandgar BP.
Pandit SS.
Tetrahedron Lett.
2003,
44:
2331
<A NAME="RM03803SS-26C">26c</A>
De Luca L.
Giacomelli G.
Taddei M.
J. Org. Chem.
2001,
66:
2534
<A NAME="RM03803SS-26D">26d</A>
De Luca L.
Giacomelli G.
Porcheddu A.
Org. Lett.
2001,
3:
1519
<A NAME="RM03803SS-26E">26e</A>
Kunishima M.
Yoshimura K.
Morigaki H.
Kawamata R.
Terao K.
Tani S.
J. Am. Chem. Soc.
2001,
123:
10760
<A NAME="RM03803SS-26F">26f</A>
Pontikis R.
Dolle V.
Guillaumel J.
Dechaux E.
Note R.
Nguyen CH.
Legraverend M.
Bisagni E.
Aubertin A.-M.
Grierson DS.
Monneret C.
J. Med. Chem.
2000,
43:
1927
<A NAME="RM03803SS-27">27</A>
Kami
ñska JE.
Kami
ñski ZJ.
Góra J.
Synthesis
1999,
593
<A NAME="RM03803SS-28">28</A>
Kami
ñski ZJ.
Paneth P.
Rudzi
ñski J.
J. Org. Chem.
1998,
63:
4238
<A NAME="RM03803SS-29">29</A>
Kamiñ
ski ZJ.
Tetrahedron Lett.
1985,
26:
2901
<A NAME="RM03803SS-30">30</A>
Garrett C.
Jiang X.
Prasad K.
Repi
è O.
Tetrahedron Lett.
2002,
43:
4161
<A NAME="RM03803SS-31">31</A>
Kami
ñski ZJ.
Synthesis
1987,
917
See, for example:
<A NAME="RM03803SS-32A">32a</A>
Inai Y.
Ousaka N.
Okabe T.
J. Am. Chem. Soc.
2003,
125:
8151
<A NAME="RM03803SS-32B">32b</A>
Venkatraman J.
Shankaramma SC.
Balaram P.
Chem. Rev.
2001,
101:
3131
<A NAME="RM03803SS-32C">32c</A>
Obrecht D.
Abrecht C.
Altorfer M.
Bohdal U.
Grieder A.
Kleber M.
Pfyffer P.
Müller K.
Helv. Chim. Acta
1996,
79:
1315
<A NAME="RM03803SS-32D">32d</A>
Di Blasio B.
Pavone V.
Saviano M.
Lombardi A.
Nastri F.
Pedone C.
Benedetti E.
Crisma M.
Anzolin M.
Toniolo C.
J. Am. Chem. Soc.
1992,
114:
6273
<A NAME="RM03803SS-32E">32e</A>
Toniolo C.
Benedetti E.
Macromolecules
1991,
24:
4004
<A NAME="RM03803SS-32F">32f</A>
Hruby VJ.
Al-Obeidi F.
Kazmierski W.
Biochem. J.
1990,
268:
249
<A NAME="RM03803SS-32G">32g</A>
Toniolo C.
Benedetti E.
ISI Atlas Sci. Biochem.
1988,
1:
225
<A NAME="RM03803SS-33A">33a</A>
Santagada V.
Fiorino F.
Perissutti E.
Severino B.
De Filippis V.
Vivenzio B.
Caliendo G.
Tetrahedron Lett.
2001,
42:
5171
<A NAME="RM03803SS-33B">33b</A>
Leibfritz D.
Haupt E.
Dubischar N.
Lachmann H.
Oekonomopulos R.
Jung G.
Tetrahedron
1982,
38:
2165
<A NAME="RM03803SS-33C">33c</A>
Balasubramanian TM.
Kendrick NCE.
Taylor M.
Marshall GR.
Hall JE.
Vodyanoy I.
Reusser F.
J. Am. Chem. Soc.
1981,
103:
6127
<A NAME="RM03803SS-34">34</A>
Frérot E.
Coste J.
Pantaloni A.
Dufour M.-N.
Jouin P.
Tetrahedron
1991,
47:
259
<A NAME="RM03803SS-35">35</A>
Kami
ñski ZJ.
Kolesi
ñska B.
Kami
ñska JE.
Góra J.
J. Org. Chem.
2001,
66:
6276
<A NAME="RM03803SS-36">36</A>
Studer A.
Jeger P.
Wipf P.
Curran DP.
J. Org. Chem.
1997,
62:
2917
<A NAME="RM03803SS-37">37</A>
Herrera V.
de Rege PJF.
Horváth IT.
Le Husebo T.
Hughes RP.
Inorg. Chem. Commun.
1998,
1:
197
<A NAME="RM03803SS-38A">38a</A>
Breed LW.
Burton WH.
Kraebel CM.
J. Org. Chem.
1965,
30:
3224
<A NAME="RM03803SS-38B">38b</A>
Breed LW.
Burton WH.
Kraebel CM.
J. Chem. Eng. Data
1965,
10:
384
<A NAME="RM03803SS-38C">38c</A>
Carignano G,
Russo A,
Savarino P,
Baratta P, and
Visca M. inventors; EP 1033368.
; Chem. Abstr.
2000, 133, 239311
<A NAME="RM03803SS-39">39</A>
Hoentjen G,
de Graaf SAG,
Bijkerk AK, and
de Jonge CRHI. inventors; US Patent 4204060.
; Chem. Abstr. 1981, 94, 15777y
<A NAME="RM03803SS-40">40</A>
The term ‘hydroxytriazine’ is used for the triazine by-product. However, energetically
favored hydroxyimino-amide equilibrium is attributed to excellent leaving group properties.
<A NAME="RM03803SS-41A">41a</A>
Kunishima M.
Kawachi C.
Hioki K.
Terao K.
Tani S.
Tetrahedron
2001,
57:
1551
<A NAME="RM03803SS-41B">41b</A>
Falchi A.
Giacomelli G.
Porcheddu A.
Taddei M.
Synlett
2000,
275
<A NAME="RM03803SS-41C">41c</A>
Kunishima M.
Kawachi C.
Morita J.
Terao K.
Iwasaki F.
Tani S.
Tetrahedron
1999,
55:
13159
<A NAME="RM03803SS-41D">41d</A>
Kunishima M.
Morita J.
Kawachi C.
Iwasaki F.
Terao K.
Tani S.
Synlett
1999,
1255
<A NAME="RM03803SS-41E">41e</A>
Kunishima M.
Kawachi C.
Iwasaki F.
Terao K.
Tani S.
Tetrahedron Lett.
1999,
40:
5327
<A NAME="RM03803SS-42">42</A>
Chiriac CI.
Onciu M.
Tibirna M.
Tanasa F.-M.
Truşcan I.
Ropot R.
Rev. Roum. Chim.
1998,
43:
31
<A NAME="RM03803SS-43">43</A>
Jones JH.
Liberek B.
Young GT.
J. Chem. Soc. C
1967,
2371
<A NAME="RM03803SS44A"></A>
Lee S.
Kanmera T.
Ayoagi H.
Izumiya N.
Int. J. Pept. Protein Res.
1979,
13:
207
<A NAME="RM03803SS44B"></A>
Lübke K.
Schröder E.
Schmichen R.
Gibian H.
Liebigs Ann. Chem.
1964,
679:
195
<A NAME="RM03803SS-45">45</A>
Kamiński ZJ.
Sci. Bull. Tech. Univ. Łódź
1996,
763:
3 ; in Polish
<A NAME="RM03803SS-46">46</A>
Kamiński ZJ.
Int. J. Pept. Protein Res.
1994,
43:
312
<A NAME="RM03803SS-47">47</A>
Visser S.
Roeloffs J.
Kerling KET.
Havinga E.
Recl. Trav. Chim. Pays-Bas
1968,
87:
559
<A NAME="RM03803SS-48">48</A>
A flask was charged with 1 (0.506 g, 0.500 mmol), 2c (0.111 g, 0.497 mmol), 3c·HCl (0.070 g, 0.50 mmol), and THF (10 mL). The mixture was cooled to 0 °C and a solution
of NMM in THF (10% v/v, 1.15 mL, 1.05 mmol) was added dropwise. The mixture was stirred
for 2 h at 0 °C. The ice bath was removed and the mixture was allowed to reach r.t.
while stirring for 14 h. Work-up similar to General Procedure gave 4c as a white solid (0.086 g, 56%).
<A NAME="RM03803SS-49A">49a</A>
Tonelli AE.
J. Am. Chem. Soc.
1973,
95:
5946
<A NAME="RM03803SS-49B">49b</A>
Breznik M.
Grdadolnik SG.
Giester G.
Leban I.
Kikelj D.
J. Org. Chem.
2001,
66:
7044
<A NAME="RM03803SS-49C">49c</A>
Fischer S.
Dunbrack RL.
Karplus M.
J. Am. Chem. Soc.
1994,
116:
11931
<A NAME="RM03803SS-49D">49d</A> For detailed NMR conformational studies of proline peptides, see for example:
Madalengoitia JS.
J. Am. Chem. Soc.
2000,
122:
4986
<A NAME="RM03803SS-50">50</A>
Ben-Ishai D.
Berger A.
J. Org. Chem.
1952,
17:
1564
<A NAME="RM03803SS-51">51</A>
4-{4,6-Bis[(heptadecafluorononyl)oxy]-1,3,5-triazin-2-yl}-4-methylmorpholinium chloride
(5) was isolated by filtration and characterized by 1H NMR spectroscopy. 1H NMR (acetone-d
6): δ = 5.20 (t, J = 13.8 Hz, 4 H, CF2CH2O), 3.91 (t, J = 4.8 Hz, 4 H, NCH2CH
2O), 3.76 (t, J = 4.8 Hz, 4 H, NCH
2CH2O), 2.12 (s, 3 H, CH3).
<A NAME="RM03803SS-52">52</A> Vibration assignments for the C3N3 ring (D3h;E¢ in-plane stretching; A2¢¢: out-of-plane bending) based on:
Herman TS.
Appl. Spectrosc.
1966,
20:
159
<A NAME="RM03803SS-53">53</A>
Peak assigned to traces of 2,4,6,-tris[(heptadecafluorononyl)oxy]-1,3,5-triazine.
<A NAME="RM03803SS-54">54</A>
Hoogwater DA.
Peereboom M.
Tetrahedron
1990,
46:
5325
<A NAME="RM03803SS-55">55</A>
‘L’ and ‘R’ denote ‘left’ and ‘right’ amino acid fragments for the Cbz-Aaa- and Aaa-OMe
fragments, where assignments were possible.
<A NAME="RM03803SS-56">56</A>
‘*’ denotes the chemical shift for the minor isomer.
<A NAME="RM03803SS-57">57</A>
Okada Y.
Okinaka M.
Yagyu M.
Watabe K.
Sano K.
Kakiuchi Y.
Chem. Pharm. Bull.
1976,
24:
3081
<A NAME="RM03803SS-58">58</A>
Ipso signal was not observed.
