G. R. Krishnan, K. Sreekumar
FULL PAPER
CH ) ppm. FTIR (KBr): ν=2200 (CN), 1614 (C=C) cm–1. See
Table, Entry 4.
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˜
3
2-(2-Hydroxy-1,2-diphenylethylidene)malononitrile: Colourless crys-
tals (1301.45 mg, 100%). M.p. 133 °C. 1H NMR (400 MHz, [D6]
DMSO, 25 °C): δ = 7.9 (s, 2 H, phenyl), 7.5–7.2 (m, 8 H, phenyl),
3.3 (s, 1 H, CH), 2.5 (s, 1 H, OH) ppm. FTIR (KBr): ν = 3413
˜
(OH), 2216 (CN), 1599 (C=C) cm–1. See Table, Entry 15.
Ethyl (E)-2-Cyano-3-(4-hydroxyphenyl)prop-2-enoate: Yellow crys-
tals (1086.1 mg, 100%). M.p. 168–169 °C (ref.[5] 169–170 °C). 1H
NMR (300 MHz, CDCl3, 25 °C): δ = 8.2 (s, 1 H, CH), 7.9 (d, J =
8.0 Hz, 2 H, phenyl), 7.0 (d, J = 8.0 Hz, 2 H, phenyl), 4.4 (q, J =
7.0 Hz, 2 H, CH2), 1.4 (t, J = 7.0 Hz, 3 H, CH3) ppm. FTIR (KBr:
[6]
[7]
ν = 3353 (OH), 2227 (CN), 1608 (C=C), 1174 (C–C–O), 1030 (O–
˜
C–C) cm–1. See Table, Entry 21.
Diethyl 2-(4-Methoxybenzylidene)malonate: Colourless liquid
(1349.75 mg, 97%). 1H NMR (300 MHz, CDCl3, 25 °C): δ = 7.6
(s, 1 H, CH), 7.3 (d, J = 8.0 Hz, 2 H, phenyl), 6.8 (d, J = 8.0 Hz,
2 H, phenyl), 4.4 (q, J = 7.0 Hz, 2 H, CH2), 4.3 (q, J = 7.0 Hz, 2
H, CH2), 3.8 (s, 3 H, OCH3), 1.4 (t, J = 7.0 Hz, 3 H, CH3), 1.3 (t,
[8]
J = 7.0 Hz, 3 H,CH ) ppm. FTIR (KBr): ν = 1728 (C=O), 1283
˜
3
(C–C–O), 1112 (O–C–C) cm–1. See Table, Entry 30.
Supporting Information (see footnote on the first page of this arti-
cle): Characterization data for all the olefins prepared and
MALDi-TOF-MS spectrum of the third-generation dendrimer.
[9]
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Acknowledgments
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The authors thank the Defence Research and Development Or-
ganization, India for the financial support and Thermax India Ltd.
Thane for the gift sample of chloromethyl polystyrene.
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The generation number was assigned according to
refs.[10,12b–12e]
Received: May 28, 2008
Published Online: August 26, 2008
4768
www.eurjoc.org
© 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2008, 4763–4768