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Analytical Data
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N
-(Diphenylmethylene)-1-(pyrrolidin-1-yl)ethenamine
(3)
IR (KBr pellet): 3450, 3059, 2972, 2877, 1715,
1628 (s), 1490, 1445, 1341, 1317, 1278, 1239, 1183, 1157, 1074, 1030,
969, 919, 872, 783, 765, 699, 639 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 7.68
(d, 2 H, ArH), 7.50-7.30 (m, 8 H, ArH), 4.94 (s, 1 H, =CHH), 4.70 (s, 1 H, =CHH), 3.51 (m,
2 H, NCH2),
3.29 (m, 2 H, NCH2), 1.81-1.76 (m, 4 H, NCH2CH
2). ¹³C
NMR (100 MHz, CDCl3): δ = 169.1,
166.1, 151.5, 139.2, 136.2, 132.6, 131.0, 130.2, 129.5, 129.2, 129.0,
128.4, 128.3, 128.1, 126.1, 105.8 (C=CHH),
48.9 (NCH2), 46.0 (NCH2), 26.4 (NCH2
CH2), 24.2 (NCH2
CH2). MS (ESI-TOF): m/z = 305.2 [M + H]+.
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Analytical Data
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IR
(KBr pellet): 3058, 3027, 2925, 2850,, 2603, 2359, 1817, 1726, 1662,
1631 (C=N), 1578, 1550, 1531, 1490, 1446, 1363, 1313, 1285,
1230, 1209, 1065, 1028, 963, 941, 919, 869, 799, 758, 692, 643,
561, 535 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 7.87-7.84
(m, 2 H, ArH), 7.61-7.57 (m, 4 H, ArH), 7.49-7.42
(m, 3 H, ArH), 7.36-7.31 (m, 4 H, ArH), 7.29-7.24
(m, 2 H, ArH), 5.19 (s, 2 H, CH2). ¹³C
NMR (100 MHz, CDCl3): δ = 166.9
(C=N), 144.2, 131.7, 131.1, 128.9, 128.3, 128.2, 127.8,
126.4, 113.9 (CPh2), 74.2 (CH2). MS (ESI-TOF): m/z = 300.2 [M + H]+.
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Typical Experimental
Procedure for the Synthesis of 2-Azadienes: Benzhydrylidene-[1-(4-methoxyphenyl)-vinyl]amine
(6d)
A solution of imine 4d (200
mg, 0.634 mmol, 1 equiv) in anhyd DMF (6.3 mL) was placed under
a dry air atmosphere. A suspension of NaH (84 mg of a 60% dispersion
in mineral oil, 2.1 mmol, 3.3 equiv) in anhyd DMF (2.1 mL) was added, and
the reaction mixture was stirred at r.t. for 2 d. Cold H2O was
then added, the aqueous layer was extracted three times with CH2Cl2 and
the combined organic layers dried over MgSO4. After filtration
and concentration under vacuum, the residue obtained was purified
by column chromatography (silica gel, 96:4 cyclohexane-EtOAc
containing 4% Et3N), to give 2-azadiene 6d as an off-white solid (129 mg, 65%); mp
137-139 ˚C. IR (KBr pellet): 3052, 3021,
2965, 2929, 2837, 2046, 1960, 1901, 1820, 1660, 1622, 1604, 1569, 1509,
1443, 1414, 1312, 1291, 1249, 1178, 1150, 1121, 1094, 1073, 1028,
998, 966, 938, 834, 812, 788, 770, 746, 700, 670, 647, 615, 579,
553 cm-¹. ¹H NMR
(400 MHz, CDCl3): δ = 7.79-7.75
(m, 2 H, ArH), 7.46-7.44 (m, 3 H, ArH), 7.42-7.38
(m, 2 H, ArH), 7.34-7.27 (m, 3 H, ArH), 7.13-7.09
(m, 2 H, ArH), 6.86-6.82 (m, 2 H, ArH), 4.70 (s, 1 H, CHH), 4.03 (s, 1 H, CHH),
3.80 (s, 3 H, OCH3). ¹³C NMR
(100 MHz, CDCl3): δ = 167.5
(C=N), 159.6, 154.4, 139.4, 136.2, 130.9, 130.8, 130.2,
129.4, 128.8, 128.6, 128.5, 128.4, 128.3, 128.3, 127.9, 126.9, 113.7,
94.0 (CH2), 55.4 (OCH3). HRMS (ESI-TOF): m/z calcd for C22H20NO [M + H]+:
314.1545; found: 314.1547.
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