Synthesis of Uniform, Non-Natural Oligomers

Nadja Franz; Georg Kreutzer; Harm-Anton Klok

doi:10.1055/s-2006-944221

ACCOUNT

Synthesis of Uniform, Non-Natural Oligomers

Nadja Franz, Georg Kreutzer, Harm-Anton Klok*
Ecole Polytechnique Fédérale de Lausanne (EPFL), Institut des Matériaux, Laboratoire des Polymères, Bâtiment MX-D, 1015 Lausanne, Switzerland
Fax: +41(21)6935650; e-Mail: harm-anton.klok@epfl.ch;

Abstract

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Abstract

Oligomers with well-defined chain lengths are of interest as foldamers, are important as model compounds for high-molecular-weight polymers and find application in electrooptic and sensory devices. This account presents an overview of the strategies that are available for the synthesis of eight important classes of uniform oligomers. The continuous refinement of the synthetic methods allows the preparation of ever longer oligomers in higher yields and also makes it possible to introduce special functional groups. These improvements could lead to materials with new or improved properties and underline the importance of synthetic organic chemistry for the development of new functional materials.

1 Introduction
2 Synthetic Strategies
3 Alkanes - Oligoenes - Oligoynes
4 Oligoesters
5 Oligoethers
6 Oligo(phenylene)s
7 Oligo(phenylene vinylene)s
8 Oligo(phenylene ethynylene)s
9 Oligopyridines - Oligo(pyridine-pyrimidine)s
10 Oligothiophenes
11 Conclusions and Outlook

Key words

materials - oligomers - polymers - solid-phase synthesis - supramolecular chemistry

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References

<A NAME="RA41706ST-1">1</A> Van Hest JCM. Tirrell DA. Chem. Commun. 2001, 1897

<A NAME="RA41706ST-2">2</A> Merrifield B. Methods Enzymol. 1997, 289: 3

<A NAME="RA41706ST-3">3</A> Fields GB. Noble RL. Int. J. Pept. Protein Res. 1990, 35: 161

<A NAME="RA41706ST-4">4</A> Heitz W. Chem. Ztg. 1986, 110: 385

<A NAME="RA41706ST-5">5</A> Zahn H. Gleitsman B. Angew. Chem., Int. Ed. Engl. 1963, 2: 410

<A NAME="RA41706ST-6">6</A> Hatada K. Kitayama T. Ute K. Nishiura T. J. Polym. Sci., Part A: Polym. Chem. 2004, 42: 416

<A NAME="RA41706ST-7">7</A> Hatada K. Kitayama T. Ute K. Nishiura T. Macromol. Rapid Commun. 2004, 25: 1447

<A NAME="RA41706ST-8">8</A> Cubberley MS. Iverson BL. Curr. Opin. Chem. Biol. 2001, 5: 650

<A NAME="RA41706ST-9">9</A> Gellman SH. Acc. Chem. Res. 1998, 31: 173

<A NAME="RA41706ST-10">10</A> Hill DJ. Mio MJ. Prince RB. Hughes TS. Moore JS. Chem. Rev. 2001, 101: 3893

<A NAME="RA41706ST-11">11</A> Moore JS. Prince RB. Nonbiological Sequence-Specific Oligomers by Repetitive Synthesis, In Synthesis of Polymers Schlüter AD. Wiley-VCH; Weinheim: 1998.

<A NAME="RA41706ST-12">12</A> Ungar G. Stejny J. Keller A. Bidd I. Whiting MC. Science 1985, 229: 386

<A NAME="RA41706ST-13">13</A> Boda E. Ungar G. Brooke GM. Burnett S. Mohammed S. Proctor D. Whiting MC. Macromolecules 1997, 30: 4674

<A NAME="RA41706ST-14">14</A> Paynter OI. Simmonds DJ. Whiting MC. J. Chem. Soc., Chem. Commun. 1982, 1165

<A NAME="RA41706ST-15">15</A> Bidd I. Whiting MC. J. Chem. Soc., Chem. Commun. 1985, 543

<A NAME="RA41706ST-16">16</A> Brooke GM. Burnett S. Mohammed S. Proctor D. Whiting MC. J. Chem. Soc., Perkin Trans. 1 1996, 1635

<A NAME="RA41706ST-17">17</A> Brooke GM. Farren C. Harden A. Whiting MC. Polymer 2001, 42: 2777

<A NAME="RA41706ST-18">18</A> Lee KS. Wegner G. Makromol. Chem., Rapid Commun. 1985, 6: 203

<A NAME="RA41706ST-19">19</A> Martin RE. Diederich F. Angew. Chem. Int. Ed. 1999, 38: 1350

<A NAME="RA41706ST-20">20</A> Spangler CW. McCoy RK. Dembek AA. Sapochak LS. Gates BD. J. Chem. Soc., Perkin Trans. 1 1989, 151

<A NAME="RA41706ST-21">21</A> Spangler CW. Liu P.-K. Dembek AA. Havelka KO. J. Chem. Soc., Perkin Trans. 1 1991, 799

<A NAME="RA41706ST-22">22</A> Duhamel L. Duhamel P. Plé G. Ramondenc Y. Tetrahedron Lett. 1993, 34: 7399

<A NAME="RA41706ST-23">23</A> Kiehl A. Eberhardt A. Adam M. Enkelmann V. Müllen K. Angew. Chem., Int. Ed. Engl. 1992, 31: 1588

<A NAME="RA41706ST-24">24</A> Zeng F. Negishi E. Org. Lett. 2002, 4: 703

<A NAME="RA41706ST-25">25</A> Schwab PFH. Levin MD. Michl J. Chem. Rev. 1999, 99: 1863

<A NAME="RA41706ST-26">26</A> Siemsen P. Livingston RC. Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2633

<A NAME="RA41706ST-27">27</A> Armitage JB. Jones ERH. Whiting MC. J. Chem. Soc. 1951, 44

<A NAME="RA41706ST-28">28</A> Cook CL. Jones ERH. Whiting MC. J. Chem. Soc. 1952, 2883

<A NAME="RA41706ST-29">29</A> Behr OM. Eglinton G. Galbraith AR. Raphael RA. J. Chem. Soc. 1960, 3614

<A NAME="RA41706ST-30">30</A> Hay AS. J. Org. Chem. 1962, 27: 3320

<A NAME="RA41706ST-31">31</A> Eastmond R. Walton DRM. Tetrahedron 1972, 28: 4591

<A NAME="RA41706ST-32">32</A> Eastmond R. Johnson TR. Walton DRM. Tetrahedron 1972, 28: 4601

<A NAME="RA41706ST-33">33</A> Rubin Y. Lin SS. Knobler CB. Anthony J. Boldi AM. Diederich F. J. Am. Chem. Soc. 1991, 113: 6943

<A NAME="RA41706ST-34">34</A> Bartik T. Bartik B. Brady M. Dembinski R. Gladysz JA. Angew. Chem., Int. Ed. Engl. 1996, 35: 414

<A NAME="RA41706ST-35">35</A> Peters TB. Bohling JC. Arif AM. Gladysz JA. Organometallics 1999, 18: 3261

<A NAME="RA41706ST-36">36</A> Dembinski R. Bartik T. Bartik B. Jaeger M. Gladysz JA. J. Am. Chem. Soc. 2000, 122: 810

<A NAME="RA41706ST-37">37</A> Mohr W. Stahl J. Hampel F. Gladysz JA. Chem. Eur. J. 2003, 9: 3324

<A NAME="RA41706ST-38">38</A> Zheng Q. Gladysz JA. J. Am. Chem. Soc. 2005, 127: 10508

<A NAME="RA41706ST-39">39</A> Xu GL. Wang CY. Ni YH. Goodson TG. Ren T. Organometallics 2005, 24: 3247

<A NAME="RA41706ST-40">40</A> Gibtner T. Hampel F. Gisselbrecht JP. Hirsch A. Chem. Eur. J. 2002, 8: 408

<A NAME="RA41706ST-41">41</A> Eisler S. Slepkov AD. Elliott E. Luu T. McDonald R. Hegmann FA. Tykwinski RR. J. Am. Chem. Soc. 2005, 127: 2666

<A NAME="RA41706ST-42">42</A> Hässlin H.-W. Dröscher M. Wegner G. Makromol. Chem. 1980, 181: 301

<A NAME="RA41706ST-43">43</A> Pénisson R. Zahn H. Makromol. Chem. 1970, 133: 25

<A NAME="RA41706ST-44">44</A> Huang B. Hermes ME. J. Polym. Sci., Part A: Polym. Chem. 1995, 33: 1419

<A NAME="RA41706ST-45">45</A> Lengweiler UD. Fritz MG. Seebach D. Helv. Chim. Acta 1996, 79: 670

<A NAME="RA41706ST-46">46</A> Seebach D. Fritz MG. Int. J. Biol. Macromol. 1999, 25: 217

<A NAME="RA41706ST-47">47</A> Krell CM. Seebach D. Eur. J. Org. Chem. 2000, 1207

<A NAME="RA41706ST-48">48</A> Brooke GM. Cameron NR. MacBride JAH. Whiting MC. Polymer 2002, 43: 1139

<A NAME="RA41706ST-49">49</A> Williams JB. Chapman TM. Hercules DM. Macromolecules 2003, 36: 3898

<A NAME="RA41706ST-50">50</A> Kuisle O. Quinoa E. Riguera R. J. Org. Chem. 1999, 64: 8063

<A NAME="RA41706ST-51">51</A> Brummer O. Clapham B. Janda KD. Tetrahedron Lett. 2001, 42: 2257

<A NAME="RA41706ST-52">52</A> Kochendoerfer GG. Chen S.-Y. Mao F. Cressman S. Traviglia S. Shao H. Hunter CL. Low DW. Cagle EN. Carnevali M. Gueriguian V. Keogh PJ. Porter H. Stratton SM. Wiedeke MC. Wilken J. Tang J. Levy JJ. Miranda LP. Crnogorac MM. Kalbag S. Botti P. Schindler-Horvat J. Savatski L. Adamson JW. Kung A. Kent SBH. Bradburne JA. Science 2003, 299: 884

<A NAME="RA41706ST-53">53</A> Burns CJ. Field LD. Morgan J. Petteys BJ. Prashar J. Ridley DD. Sandanayake KRAS. Vignevich V. Aust. J. Chem. 2001, 54: 431

<A NAME="RA41706ST-54">54</A> Teo HH. Mobbs RH. Booth C. Eur. Polym. J. 1982, 18: 541

<A NAME="RA41706ST-55">55</A> Kinugasa S. Hayashi H. Hattori S. Polym. J. 1990, 22: 1059

<A NAME="RA41706ST-56">56</A> Kinugasa S. Takatsu A. Nakanishi H. Nakahara H. Hattori S. Macromolecules 1992, 25: 4848

<A NAME="RA41706ST-57">57</A> Keegstra EMD. Zwikker JW. Roest MR. Jenneskens LW. J. Org. Chem. 1992, 57: 6678

<A NAME="RA41706ST-58">58</A> Malanga C. Spassky N. Menicagli R. Chiellini E. Synth. Commun. 1982, 12: 67

<A NAME="RA41706ST-59">59</A> Malanga C. Spassky N. Menicagli R. Chiellini E. Polym. Bull. 1983, 9: 328

<A NAME="RA41706ST-60">60</A> Henderson HC. Sherrington DC. Gough A. Polymer 1994, 35: 2867

<A NAME="RA41706ST-61">61</A> Knuf EC. Jiang JK. Gin MS. J. Org. Chem. 2003, 68: 9166

<A NAME="RA41706ST-62">62</A> Percec V. Asandei AD. Macromolecules 1997, 30: 7701

<A NAME="RA41706ST-63">63</A> Berresheim AJ. Müller M. Müllen K. Chem. Rev. 1999, 99: 1747

<A NAME="RA41706ST-64">64</A> Kovacic P. Jones MB. Chem. Rev. 1987, 87: 357

<A NAME="RA41706ST-65">65</A> Kraft A. Grimsdale AC. Holmes AB. Angew. Chem. Int. Ed. 1998, 37: 402

<A NAME="RA41706ST-66">66</A> Reddinger JL. Reynolds JR. Adv. Polym. Sci. 1999, 145: 57

<A NAME="RA41706ST-67">67</A> Grimsdale AC. Müllen K. Angew. Chem. Int. Ed. 2005, 44: 5592

<A NAME="RA41706ST-68">68</A> Scherf U. Top. Curr. Chem. 1999, 201: 163

<A NAME="RA41706ST-69">69</A> Deeg O. Kirsch P. Pauluth D. Bäuerle P. Chem. Commun. 2002, 2762

<A NAME="RA41706ST-70">70</A> Sidorov V. Douglas T. Dzekunov SM. Abdallah D. Ghebremariam B. Roepe PD. Matile S. Chem. Commun. 1999, 1429

<A NAME="RA41706ST-71">71</A> Winum J.-Y. Matile S. J. Am. Chem. Soc. 1999, 121: 7961

<A NAME="RA41706ST-72">72</A> Baumeister B. Matile S. Chem. Commun. 2000, 913

<A NAME="RA41706ST-73">73</A> Baumeister B. Sakai N. Matile S. Angew. Chem. Int. Ed. 2000, 39: 1955

<A NAME="RA41706ST-74">74</A> Pummerer R. Bittner K. Ber. Dtsch. Chem. Ges. 1924, 57: 84

<A NAME="RA41706ST-75">75</A> Pummerer R. Seligsberger L. Ber. Dtsch. Chem. Ges. 1931, 64: 2477

<A NAME="RA41706ST-76">76</A> Nozaki T. Tamura M. Harada Y. Saito K. Bull. Chem. Soc. Jpn. 1960, 33: 1329

<A NAME="RA41706ST-77">77</A> Kern W. Seibel M. Wirth HO. Makromol. Chem. 1959, 29: 164

<A NAME="RA41706ST-78">78</A> Cade JA. Pilbeam A. J. Chem. Soc. 1964, 114

<A NAME="RA41706ST-79">79</A> Heitz W. Ullrich R. Makromol. Chem. 1966, 98: 29

<A NAME="RA41706ST-80">80</A> Mayer F. Schiffner R. Ber. Dtsch. Chem. Ges. 1932, 65: 1337

<A NAME="RA41706ST-81">81</A> Müller E. Töpel T. Ber. Dtsch. Chem. Ges. 1939, 72: 273

<A NAME="RA41706ST-82">82</A> Kern W. Gruber W. Wirth HO. Makromol. Chem. 1960, 37: 198

<A NAME="RA41706ST-83">83</A> Kovacic P. Lange RM. J. Org. Chem. 1964, 29: 2416

<A NAME="RA41706ST-84">84</A> Laird T. Ollis WD. Sutherland IO. J. Chem. Soc., Perkin Trans. 1 1980, 1473

<A NAME="RA41706ST-85">85</A> Unroe MR. Reinhardt BA. Synthesis 1987, 981

<A NAME="RA41706ST-86">86</A> Subramaniam G. Gilpin RK. Synthesis 1992, 1232

<A NAME="RA41706ST-87">87</A> Kauffman JM. Synthesis 1999, 918

<A NAME="RA41706ST-88">88</A> Galda P. Rehahn M. Synthesis 1996, 614

<A NAME="RA41706ST-89">89</A> Liess P. Hensel V. Schlüter AD. Liebigs Ann. 1996, 1037

<A NAME="RA41706ST-90">90</A> Read MW. Escobedo JO. Willis DM. Beck PA. Strongin RM. Org. Lett. 2000, 2: 3201

<A NAME="RA41706ST-91">91</A> McDonald FE. Smolentsev V. Org. Lett. 2002, 4: 745

<A NAME="RA41706ST-92">92</A> Tour JM. Chem. Rev. 1996, 96: 537

<A NAME="RA41706ST-93">93</A> Tour JM. Acc. Chem. Res. 2000, 33: 791

<A NAME="RA41706ST-94">94</A> Schenk R. Gregorius H. Meerholz K. Heinze J. Müllen K. J. Am. Chem. Soc. 1991, 113: 2634

<A NAME="RA41706ST-95">95</A> Heinze J. Mortensen J. Müllen K. Schenk R. J. Chem. Soc., Chem. Commun. 1987, 701

<A NAME="RA41706ST-96">96</A> Gregorius H. Baumgarten M. Reuter R. Tyutyulkov N. Müllen K. Angew. Chem., Int. Ed. Engl. 1992, 31: 1653

<A NAME="RA41706ST-97">97</A> Meier H. Gerold J. Kolshorn H. Baumann W. Bletz M. Angew. Chem. Int. Ed. 2001, 41: 292

<A NAME="RA41706ST-98">98</A> Jørgensen M. Krebs FC. J. Org. Chem. 2004, 69: 6688

<A NAME="RA41706ST-99">99</A> Maddux T. Li W. Yu L. J. Am. Chem. Soc. 1997, 119: 844

<A NAME="RA41706ST-100">100</A> Chan TL. Chow HF. Fong S. Leung MK. Tu JG. J. Chem. Soc., Chem. Commun. 1994, 1919

<A NAME="RA41706ST-101">101</A> Siegrist AE. Helv. Chim. Acta 1967, 50: 906

<A NAME="RA41706ST-102">102</A> Siegrist AE. Liechti P. Meyer HR. Weber K. Helv. Chim. Acta 1969, 52: 2521

<A NAME="RA41706ST-103">103</A> Meier H. Ickenroth D. Eur. J. Org. Chem. 2002, 1745

<A NAME="RA41706ST-104">104</A> Zheng J. Swager TM. Adv. Polym. Sci. 2005, 177: 151

<A NAME="RA41706ST-105">105</A> Bunz UHF. Adv. Polym. Sci. 2005, 177: 1

<A NAME="RA41706ST-106">106</A> Ray CR. Moore JS. Adv. Polym. Sci. 2005, 177: 91

<A NAME="RA41706ST-107">107</A> Blatchly RA. Tew GN. J. Org. Chem. 2003, 68: 8780

<A NAME="RA41706ST-108">108</A> Shotwell S. Windscheif PM. Smith MD. Bunz UHF. Org. Lett. 2004, 6: 4151

<A NAME="RA41706ST-109">109</A> Zhang J. Moore JS. Xu Z. Aguirre RA. J. Am. Chem. Soc. 1992, 114: 2273

<A NAME="RA41706ST-110">110</A> Zhang J. Pesak DJ. Ludwick JL. Moore JS. J. Am. Chem. Soc. 1994, 116: 4227

<A NAME="RA41706ST-111">111</A> Stone MT. Moore JS. Org. Lett. 2004, 6: 469

<A NAME="RA41706ST-112">112</A> Schumm JS. Pearson DL. Tour JM. Angew. Chem., Int. Ed. Engl. 1994, 33: 1360

<A NAME="RA41706ST-113">113</A> Jones L. Schumm JS. Tour JM. J. Org. Chem. 1997, 62: 1388

<A NAME="RA41706ST-114">114</A> Jones TV. Blatchly RA. Tew GN. Org. Lett. 2003, 5: 3297

<A NAME="RA41706ST-115">115</A> Ziener U. Godt A. J. Org. Chem. 1997, 62: 6137

<A NAME="RA41706ST-116">116</A> Kukula H. Veit S. Godt A. Eur. J. Org. Chem. 1999, 277

<A NAME="RA41706ST-117">117</A> Lavastre O. Ollivier L. Dixneuf PH. Sibandhit S. Tetrahedron 1996, 52: 5495

<A NAME="RA41706ST-118">118</A> Zhou CZ. Liu T. Xu JM. Chen ZK. Macromolecules 2003, 36: 1457

<A NAME="RA41706ST-119">119</A> Nierengarten J.-F. Gu T. Hadziioannou G. Tsamouras D. Krasnikov V. Helv. Chim. Acta 2004, 87: 2948

<A NAME="RA41706ST-120">120</A> Nelson JC. Young JK. Moore JS. J. Org. Chem. 1996, 61: 8160

<A NAME="RA41706ST-121">121</A> Young JK. Nelson JC. Moore JS. J. Am. Chem. Soc. 1994, 116: 10841

<A NAME="RA41706ST-122">122</A> Huang S. Tour JM. J. Am. Chem. Soc. 1999, 121: 4908

<A NAME="RA41706ST-123">123</A> Huang S. Tour JM. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1998, 39: 525

<A NAME="RA41706ST-124">124</A> Constable EC. Tetrahedron 1992, 48: 10013

<A NAME="RA41706ST-125">125</A> Tschierske C. Angew. Chem. Int. Ed. 2000, 39: 2454

<A NAME="RA41706ST-126">126</A> Constable EC. Prog. Inorg. Chem. 1994, 42: 67

<A NAME="RA41706ST-127">127</A> Albrecht M. Chem. Rev. 2001, 101: 3457

<A NAME="RA41706ST-128">128</A> Hannon MJ. Childs LJ. Supramol. Chem. 2004, 16: 7

<A NAME="RA41706ST-129">129</A> Burstall FH. J. Chem. Soc. 1938, 1662

<A NAME="RA41706ST-130">130</A> Frank RL. Riener EF. J. Am. Chem. Soc. 1950, 72: 4182

<A NAME="RA41706ST-131">131</A> Kröhnke F. Synthesis 1976, 1

<A NAME="RA41706ST-132">132</A> Constable EC. Smith DR. Tetrahedron 1997, 53: 1715

<A NAME="RA41706ST-133">133</A> Potts KT. Bull. Soc. Chim. Belg. 1990, 99: 741

<A NAME="RA41706ST-134">134</A> Potts KT. Cipullo MJ. Ralli P. Theodoridis G. J. Org. Chem. 1982, 47: 3027

<A NAME="RA41706ST-135">135</A> Bassani DM. Lehn J.-M. Bull. Soc. Chim. Fr. 1997, 134: 897

<A NAME="RA41706ST-136">136</A> Bassani DM. Lehn J.-M. Baum G. Fenske D. Angew. Chem., Int. Ed. Engl. 1997, 36: 1845

<A NAME="RA41706ST-137">137</A> Ohkita M. Lehn J.-M. Baum G. Fenske D. Chem. Eur. J. 1999, 5: 3471

<A NAME="RA41706ST-138">138</A> Newkome GR. Patri AK. Holder E. Schubert US. Eur. J. Org. Chem. 2004, 235

<A NAME="RA41706ST-139">139</A> Lehmann U. Henze O. Schlüter AD. Chem. Eur. J. 1999, 5: 854

<A NAME="RA41706ST-140">140</A> Chotalia R. Constable EC. Neuburger M. Smith DR. Zehnder M. J. Chem. Soc., Dalton Trans. 1996, 4207

<A NAME="RA41706ST-141">141</A> Cárdenas DJ. Sauvage J.-P. Synlett 1996, 916

<A NAME="RA41706ST-142">142</A> Hanan GS. Lehn J.-M. Kyritsakas N. Fischer J. J. Chem. Soc., Chem. Commun. 1995, 765

<A NAME="RA41706ST-143">143</A> Benaglia M. Ponzini F. Woods CR. Siegel JS. Org. Lett. 2001, 3: 967

<A NAME="RA41706ST-144">144</A> Roncali J. Chem. Rev. 1992, 92: 711

<A NAME="RA41706ST-145">145</A> McCullough RD. Adv. Mater. 1998, 10: 93

<A NAME="RA41706ST-146">146</A> Mitschke U. Bäuerle P. J. Mater. Chem. 2000, 10: 1471

<A NAME="RA41706ST-147">147</A> McQuade DT. Pullen AE. Swager TM. Chem. Rev. 2000, 100: 2537

<A NAME="RA41706ST-148">148</A> Sease JW. Zechmeister L. J. Am. Chem. Soc. 1947, 69: 270

<A NAME="RA41706ST-149">149</A> Asano T. Ito S. Saito N. Hatakeda K. Heterocycles 1977, 6: 317

<A NAME="RA41706ST-150">150</A> Kagan J. Arora SK. Heterocycles 1983, 20: 1937

<A NAME="RA41706ST-151">151</A> Kagan J. Arora SK. Tetrahedron Lett. 1983, 24: 4043

<A NAME="RA41706ST-152">152</A> Kagan J. Arora SK. J. Org. Chem. 1983, 48: 4317

<A NAME="RA41706ST-153">153</A> Ten Hoeve W. Wynberg H. Havinga EE. Meijer EW. J. Am. Chem. Soc. 1991, 113: 5887

<A NAME="RA41706ST-154">154</A> Tamao K. Kodama S. Nakajima I. Kumada M. Minato A. Suzuki K. Tetrahedron 1982, 38: 3347

<A NAME="RA41706ST-155">155</A> Cunningham DD. Laguren-Davidson L. Mark HB. Van Pham C. Zimmer H. J. Chem. Soc., Chem. Commun. 1987, 1021

<A NAME="RA41706ST-156">156</A> Bäuerle P. Fischer T. Bidlingmeier B. Stabel A. Rabe JP. Angew. Chem., Int. Ed. Engl. 1995, 34: 303

<A NAME="RA41706ST-157">157</A> Nakanishi H. Sumi N. Aso Y. Otsubo T. J. Org. Chem. 1998, 63: 8632

<A NAME="RA41706ST-158">158</A> Tour JM. Wu R. Macromolecules 1992, 25: 1901

<A NAME="RA41706ST-159">159</A> Kirschbaum T. Azumi R. Mena-Osteritz E. Bäuerle P. New J. Chem. 1999, 23: 241

<A NAME="RA41706ST-160">160</A> Spivey AC. Turner DJ. Turner ML. Yeates S. Org. Lett. 2002, 4: 1899

<A NAME="RA41706ST-161">161</A> Sakurai S. Goto H. Yashima E. Org. Lett. 2001, 3: 2379

<A NAME="RA41706ST-162">162</A> Malenfant PRL. Fréchet JMJ. Chem. Commun. 1998, 2657

<A NAME="RA41706ST-163">163</A> Briehn CA. Kirschbaum T. Bäuerle P. J. Org. Chem. 2000, 65: 352

<A NAME="RA41706ST-164">164</A> Briehn CA. Bäuerle P. J. Comb. Chem. 2002, 4: 457

<A NAME="RA41706ST-165">165</A> Kirschbaum T. Briehn CA. Bäuerle P. J. Chem. Soc., Perkin Trans. 1 2000, 8: 1211