Page 13 of 22
The Journal of Organic Chemistry
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5.92 (d, J = 15.9 Hz, 1H), 1.42 (s, 6H). C{1H} NMR (101 MHz, CDCl3) δ 135.7,
130.3, 129.7, 128.6, 128.0, 126.5, 123.3, 34.8, 27.6. m/z (GC-MS) = 171.
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(E)-2,2-dimethyl-4-(p-tolyl)but-3-enenitrile (Scheme 2, 3ab, known compound) 12,13
It is synthesized from 4-methylphenylene (0.5 mmol) and AIBN (0.6 mmol) basing on
General Procedures 1 and purified by column chromatography with PE/EA= 80:1 as
the eluent. 79 mg, 86% yield, light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.27 (d,
J = 7.2 Hz, 2H), 7.13 (d, J = 7.4 Hz, 2H), 6.71 (d, J = 15.8 Hz, 1H), 5.97 (d, J = 15.9
Hz, 1H), 2.33 (s, 3H), 1.52 (s, 6H). 13C{1H} NMR (101 MHz, CDCl3) δ 138.0, 132.9,
129.6, 129.3, 129.3, 126.4, 123.5, 34.8, 27.7, 21.2. m/z (GC-MS) = 185.
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(E)-4-(4-(tert-butyl)phenyl)-2,2-dimethylbut-3-enenitrile (Scheme 2, 3ac)
It is synthesized from 4-tert-butylstyrene (0.5mmol) and AIBN (0.6 mmol) basing on
General Procedures 1 and purified by column chromatography with PE/EA= 60:1 as
the eluent. 103 mg, 91% yield, orange oil. 1H NMR (400 MHz, CDCl3) δ 7.34 (q, J =
7.9 Hz, 4H), 6.74 (d, J = 15.9 Hz, 1H), 5.99 (d, J = 15.9 Hz, 1H), 1.54 (s, 6H), 1.32 (s,
9H). 13C{1H} NMR (101 MHz, CDCl3) δ 151.3, 132.9, 129.6, 129.5, 126.3, 125.6,
123.5, 34.9, 34.6, 31.2, 27.7. HRMS (ESI) m/z calcd for C16H21NNa+ [M+Na]+ :
250.1566, found 250.1568.
(E)-4-(4-methoxyphenyl)-2,2-dimethylbut-3-enenitrile (Scheme 2, 3ad, known compound) 12a
It is synthesized from 4-methoxystyrene (0.5 mmol) and AIBN (0.6 mmol) basing on
General Procedures 1 and purified by column chromatography with PE/EA= 40:1 as
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the eluent. 85 mg, 85% yield, yellow oil. H NMR (400 MHz, CDCl3) δ 7.27 (d, J =
7.7 Hz, 2H), 6.82 (d, J = 7.7 Hz, 2H), 6.65 (d, J = 15.9 Hz, 1H), 5.86 (d, J = 15.9 Hz,
1H), 3.74 (s, 3H), 1.47 (s, 6H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.4, 129.0,
128.2, 128.0, 127.6, 123.4, 113.9, 55.0, 34.6, 27.5. m/z (GC-MS) = 201.
(E)-4-(4-fluorophenyl)-2,2-dimethylbut-3-enenitrile (Scheme 2, 3ae, known compound) 12
It is synthesized from 4-fluorostyrene (0.5 mmol) and AIBN (0.6 mmol) basing on
General Procedures 1 and purified by column chromatography with PE/EA= 60:1 as
the eluent. 81 mg, 86% yield, light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.25 (t,
J = 5.9 Hz, 2H), 6.92 (t, J = 7.9 Hz, 2H), 6.62 (d, J = 15.9 Hz, 1H), 5.85 (d, J = 15.9
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Hz, 1H), 1.43 (s, 6H). C{1H} NMR (101 MHz, CDCl3) δ 162.4 (d, J = 247.6 Hz),
131.8 (d, J = 3.2 Hz), 130.1 (d, J = 2.0 Hz), 128.6, 128.0 (d, J = 8.1 Hz), 123.3, 115.5
(d, J = 21.7 Hz), 34.8, 27.5. m/z (GC-MS) = 189.
(E)-4-(4-chlorophenyl)-2,2-dimethylbut-3-enenitrile (Scheme 2, 3af, known compound) 12a,13
It is synthesized from 4-chloroestyrene (0.5 mmol) and AIBN (0.6 mmol) basing on
General Procedures 1 and purified by column chromatography with PE/EA= 60:1 as
the eluent. 92 mg, 90% yield, yellowish white oil. 1H NMR (400 MHz, CDCl3) δ 7.28
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(s, 4H), 6.70 (d, J = 15.9 Hz, 1H), 6.00 (d, J = 15.9 Hz, 1H), 1.52 (s, 6H). C{1H}
NMR (101 MHz, CDCl3) δ 134.1, 133.6, 130.9, 128.7, 128.5, 127.7, 123.1, 34.8, 27.4.
m/z (GC-MS) = 205.
(E)-2,2-dimethyl-4-(m-tolyl)but-3-enenitrile (Scheme 2, 3ag)
It is synthesized 3-methylphenylene (0.5 mmol) and AIBN (0.6 mmol) basing on
General Procedures 1 and purified by column chromatography with PE/EA= 80:1 as
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the eluent. 77 mg, 83% yield, light yellow oil. H NMR (400 MHz, CDCl3) δ 7.28 –
7.16 (m, 3H), 7.11 (d, J = 7.0 Hz, 1H), 6.75 (d, J = 15.9 Hz, 1H), 6.04 (d, J = 15.9 Hz,
1H), 2.37 (s, 3H), 1.55 (s, 6H). 13C{1H} NMR (101 MHz, CDCl3) δ 138.1, 135.6,
130.1, 129.8, 128.8, 128.5, 127.1, 123.6, 123.4, 34.8, 27.6, 21.3. HRMS (ESI) m/z
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