Organic Reactions Volume 4 - Sciencemadness Dot Org

52 ORGANIC REACTIONS
TABLE V—Continued
ADDUCTS FBOM MALEIC ANHYDRIDE WITH AROMATIC COMPOUNDS
Diene
cis-Isoeugenol ethyl ether
2,3-Dimethoxy-l-propenylbenzene
l~(3',4'-Methylenedioxyphenyl)-
1-pentene
MethyKJ,4~methylenedioxyphenyIacetylene
(piperonylallylene)
as-Diphenylethylene
Indene
1-Vinylnaphthalene
l-Vinylnaphthalene
1-Vinylnaphthalene
2-Vinylnaphthalene
1-Propenylnaphthalene
l-Vinyl-6-methoxynaphthalene
l-Vinyl-6-methoxynaphthalene
l-(a~Naphthyl)-l-cyclopentene
l-OS-NaphthyI)-l-cyclopentene
2-Methyl-3-(«-naphthyl)-l-cyclopentene
2-Methyl~l-(/S-naphthylM-cyclo~
pentene
l-(6'-Methoxy-2'-naphthyl)-l-cyolopentene
l-(6'~Methoxy-2'-naphthyl)-2-methyl-
1-cyclopentene
3-(5'~Bromo-6'-methoxy-2'naphthyl)-2-methyl-2-cyclopenten-
1-one
l-(/3-Naphthyl)-l-cyclohexene
9~Vinylphenanthrene
9-Propenylphenanthrene
9-Isopropenylphenanthrene
9-CycIopentenyIphenanthrene
9-Cyclopentenylphenanthrene
9-Styrylphenanthrene
6-Isopropenylchrysene If
Moles
Anhydride
per Mole
Diene
1.25
1.1
_
1.2
2
0.71
1
1.2
1.1
1.05
4.3
1.1
2.1
1.05
10
10
10
10
10
10
10
1.3
1.1
Ll
1.8
—
1.1
5
Xylene
Xylene
_
Xylene
Benzene
Benzene
Xylene
Solvent
Dry toluene
Dry xylene
Xylene
None
Xylene
Acetic acid
Dry xylene
None
None
None
None
None
Xylene
None
Xylene
Xylene
Xylene
Xylene
Nitrobenzene
Xylene
Acetic anhydride
Reaction Temperature
and Time
Reflux (5 hr.)
Reflux (5 hr.)
_
150° (2 hr.)
Reflux (20 hr.)
250° (5 hr.)
100° (20 min.); room
temp. (3 days)
92° (3 hr.)
100° (3 hr.)
100° (10 min.); room
temp. (7 days)
100° (6 hr.)
100° (15 min.)
Reflux (2.5 hr.)
Reflux (2 hr.)
100° (20 hr.)
100° (20 hr.)
100° (20 hr.)
100° (20 hr.)
100° (20 hr.)
Reflux (5 hr.)
100° (12 hr.)
Reflux (5 hr.)
Reflux (4 hr.)
Reflux (4 hr.)
Reflux
Reflux
Reflux (4 hr.)
Reflux (2 hr.)
Yield
%
40-50
4
10
-t
-t
22
32
§
6
77.5
30
I!
20-22
_
—
—
•—
29
41
—
10
14
58
-t
27
92.5
Ref.*
101
101
101
101
141, 154
261
262, 263
128«
264
263
415
262, 263
128 tt
264
264
264
* References 324-434 are listed on pp. 57-59.
f Adduct dehydrogenated under reaction conditions.
% Adduct is a dianhydride.
§ A 95% yield of monomeric and copolymeric product was obtained. A 57% yield of pure, aromatized
m-dimethyl ester was obtained by alkaline hydrolysis, treatment with diazomethane, and evaporative
distillation.
Il A 39% yield of aromatized monomeric and copolymeric product was obtained. A 30% overall
yield of pure, aromatized cis-dimethyl ester was obtained by alkaline hydrolysis, treatment with
diazomethane and evaporative distillation.
% Dimethyl-6-chrysenylcarbinol which was dehydrated to give 6-isopropenylchrysene under the
reaction conditions was employed.
264
264
264
269
266
265
265
265
265
321
265
143