3
22. Wang, Y.; Cai, J.; Rauscher, H.; Behm, R. J.; Goedel, W. A.
Research supported by the U.S. Department of Energy,
Office of Basic Energy Sciences, Division of Materials Sciences
and Engineering. Sandia National Laboratories is a multi-
program laboratory managed and operated by Sandia
Corporation, a wholly owned subsidiary of Lockheed Martin
Corporation, for the U.S. Department of Energy's National
Nuclear Security Administration under contract DE-AC04-
94AL85000. Certain trade names and company products are
identified in order to specify experimental procedures
Chem. Eur. J. 2005, 11, 3968
23. Cai, X.; Chorghade, M. S.; Fura, A.; Grewal, G. S.; Jauregui, K.
A.; Lounsbury, H. A.; Scannell, R. T.; Yeh, C. G.; Young, M. A.;
Yu, S. Org. Proc. R&D 1999, 3, 73.
24. General procedure: A suspension of dihalide (1 mol), furan-
protected maleimide (3 mol), K2CO3 (3 mol) and anhydrous
DMF was purged with N2 gas and stirred at 50 °C for 24 h. After
the completion of the reaction as monitored by thin-layer
chromatography (TLC), the mixture was cooled to room
temperature, diluted with ethyl acetate, washed with water and
brine, and dried (Na2SO4). Evaporation of the solvent under
reduced pressure afforded product in the indicated yields.
25. General procedure for retro-Diels-Alder reaction: A solution of
alkylated product (1 mol) in 1,1,2,2-tetrachloroethane was stirred
at 120 °C in an open flask for 12 h. After completion of the
reaction as indicated by TLC, the solvent was evaporated under
reduced pressure to afford BMI.
adequately.
In no case does such identification imply
recommendation or endorsement by the National Institute of
Standards and Technology, nor does it imply that the products
are necessarily the best available for the purpose.
References and notes
26. Spectral data: Compound 2: Semi solid, 85% yield. 1H NMR
(500 MHz, CDCl3) δ 6.65 (s, 4H), 3.63-3.66 (m, 4H), 3.57-3.60
(m, 4H), 3.51-3.55 (m, 8H); 13C NMR (125 MHz, CDCl3) δ
170.6, 134.1, 70.5, 70.0, 67.7, 37.1; IR (KBr): 3066, 1652, 1454
cm-1; ESI (M+H+): m/z 353.1. Compound 3a: White solid, 85%
yield. 1H NMR (400MHz, CDCl3) 6.67 (s, 2H), 3.73 (s, 2H);
1.
2.
Kovacic, P.; Hein, R. W. J. Am. Chem. Soc. 1959, 81,1187.
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4.
Stenzenberger, H.D. Adv. Polym. Sci. 1994, 117, 165.
Fink, J. K. “Reactive Polymers Fundamentals and Applications,”
William Academic Inc., 2005, p. 397-446.
13C NMR (100MHz, CDCl3) 170.4, 134.1, 36.5; IR (KBr):
3106, 1710, 1405 cm-1; APCI (M+H)+: 220.8. Compound 3b:
White solid, 85% yield. 1H NMR (500 MHz, CDCl3) δ 6.70 (s,
4H), 3.50 (t, 4H),1.2 (m, 2H); 13C NMR (125 MHz, CDCl3)
170.6, 134.1, 35.6, 29.7; ESI, m/z = 235 (M+H)+. Compound 3c:
White solid, 85% yield. 1H NMR (500 MHz, CDCl3) δ 6.70 (s,
4H), 3.50 (t, 4H), 1.21 (m, 4H); 13C NMR (125 MHz, CDCl3) δ
170.8, 134.0, 37.5, 28.0, 23.8; ESI, m/z = 248 (M+H)+.
5.
6.
Sava, M. J. Appl. Polym. Sci. 2002, 84, 750.
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Polymers”, Nova Science Publishers, 2008, 229.
Compound 3d: White solid, 90% yield. 1H NMR (500 MHz,
CDCl3) δ 6.70 (s, 4H), 3.50 (t, 4H), 1.60 (m, 4H), 1.21 (m, 2H);
13C NMR (125 MHz, CDCl3) δ 170.8, 134.0, 37.5, 29.7, 28.0,
23.8; ESI, m/z = 263 (M+H)+. Compound 3e: White solid, 90%
yield. 1H NMR (500 MHz, CDCl3) δ 6.70 (s, 4H), 3.50 (t, 4H),
1.60 (m, 4H), 1.21 (m, 4H); 13C NMR (125 MHz, CDCl3) 170.8,
134.0, 37.8, 29.7, 29.3, 28.4, 26.5, 22.7; ESI, m/z = 277 (M+H)+.
Compound 3f: White solid, 93% yield. 1H NMR (500 MHz,
CDCl3) δ 6.70 (s, 4H), 3.50 (t, 4H), 1.60 (m, 4H), 1.21 (m, 6H);
13C NMR (125 MHz, CDCl3) δ 170.8, 134.0, 37.8, 29.7, 29.3,
28.5, 28.4, 26.5, 22.7; ESI, m/z = 291 (M+H)+. Compound 3g:
White solid, 92% yield. 1H NMR (500 MHz, CDCl3) δ 6.70 (s,
4H), 3.50 (t, 4H), 1.50 (m, 4H), 1.21 (m, 8H); 13C NMR (125
MHz, CDCl3) δ 170.8, 134.0, 68.0, 37.8, 29.7, 29.1, 28.9, 28.4,
26.6; ESI, m/z = 305 (M+H)+. Compound 3h: White solid, 85%
yield. 1H NMR (500 MHz, CDCl3) δ 6.70 (s, 4H), 3.50 (t, 4H),
1.50 (m, 2H), 1.21 (m, 10H), 0.90 (m, 2H); 13C NMR (125 MHz,
CDCl3) δ 170.8, 134.0, 53.4, 37.9, 29.7, 29.2, 28.9, 28.5, 26.6;
ESI, m/z = 319 (M+H)+. Compound 3i: White solid, 95% yield.
1H NMR (500 MHz, CDCl3) δ 6.65 (s, 4H), 3.50 (t, 4H), 1.50 (m,
4H), 1.21 (m, 12H); 13C NMR (125 MHz, CDCl3) δ 170.8, 134,
53.3, 37.8, 29.6, 29.2, 29.0, 28.4, 26.6; ESI m/z = 333 (M+H)+.
Compound 4: 1H NMR (400 MHz, DMSO-d6) δ 7.01 (s, 4H);
4.86 (d, J = 6 Hz, 2H); 3.37-3.68 (m, 4H); 3.31 (s, 2H); 13C NMR
(100 MHz, DMSO-d6) δ 171.6, 134.9, 68.4, 49.0; IR(KBr): 3540,
2614, 1702, 1415 cm-1; ESI (M+H)+: 280.9; Mp: 205-207°C.
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