Organic Reactions Volume 4 - Sciencemadness Dot Org
Organic Reactions Volume 4 - Sciencemadness Dot Org
Organic Reactions Volume 4 - Sciencemadness Dot Org
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BIENE SYNTHESIS I 55<br />
TABLE VII—Continued<br />
ADDUCTS FROM DIENOPHILES RELATED TO MALEIC ANHYDRIDE<br />
Dienophile<br />
(Moles per Mole Diene)<br />
Fumaronitrile<br />
N-Isobutylmaleimide (0.69)<br />
N-Isobutylmaleimide (1)<br />
N-Isobutylmaleimide (1)<br />
N-Isobutylmaleimide (1)<br />
N-lsobutylmaloimide (1,05)<br />
Methylmaleic anhydride (citraconic<br />
anhydride)<br />
Citraconic anhydride (1)<br />
Citraconio anhydride<br />
Citraconic anhydride<br />
Citraconic anhydride<br />
Citraconic anhydride<br />
Citraconic anhydride (1.15)<br />
Citraconic anhydride (0.3)<br />
Citraconic anhydride (2)<br />
Citraconic anhydride (2.1)<br />
Itaoonic anhydride (0.65-0.8)<br />
Methylfumaric acid<br />
(mesaconic acid) (6)<br />
Mesaconio acid (2.5)<br />
Mesaconic acid (2.1)<br />
Dimethylmaleic anhydride (pyrocinchonic<br />
anhydride) (0.5)<br />
Pyrocinchonic anhydride (1)<br />
Pyrocinchonic anhydride (0.53)<br />
Pyrocinchonic anhydride (0.2)<br />
Pyrocinchonic anhydride (0.5)<br />
Pyrocinchonic anhydride<br />
Dichloromaleie anhydride (1.2)<br />
Dibromomaleic anhydride (0.39)<br />
Dibromomaleic anhydride (2)<br />
Dibromomaleic anhydride (1.2)<br />
Acetoxymaleic anhydride<br />
3,6-DihydrophthaIic anhydride<br />
(0.28)<br />
3,4,5,6-Tetrahydrophthalic<br />
anhydride (0.2)<br />
Butadiene<br />
Butadiene<br />
Isoprene<br />
Diene<br />
2,3-Dimethyl-l,3-butadiene<br />
Cyclopentadicne<br />
Pyrrole<br />
2-ChIoro-l,3-butadiene<br />
Cyclopentadiene<br />
22-Dihydrotachystorol<br />
BiosterOl<br />
Tachysterol acetate<br />
l-Vinyl*6-methoxy-3,4-dihydronaphthalene<br />
Anthracene<br />
Anthracene<br />
1-Vinylnaphthalene<br />
l-'VinyH-methoxynaphthalene<br />
Cyclopentadiene<br />
Anthracene<br />
1-Vinylnaphthalene<br />
l*Vinyl-6-methoxynaphthalene<br />
Butadiene<br />
Butadiene<br />
Cyclopentadiene<br />
Cyclopentadiene<br />
1,3-Cy clohexadiene<br />
1-Propenylnaphthalene<br />
Anthracene<br />
Cyclopentadiene<br />
1,3-Cy clohexadiene<br />
Anthracene<br />
Cyclopentadiene<br />
Butadiene<br />
Butadiene<br />
Solvent<br />
Toluene<br />
Water<br />
(emulsion)<br />
Water<br />
(emulsion)<br />
Water<br />
(emulsion)<br />
Water<br />
(emulsion)<br />
Water<br />
(emulsion)<br />
_<br />
Benzene<br />
Ether<br />
—<br />
—<br />
_<br />
Benzene<br />
None<br />
Dry toluene<br />
Propionic<br />
acid<br />
Propionic<br />
acid<br />
Benzene<br />
Propionic<br />
acid<br />
Propionic<br />
acid<br />
Propionic<br />
acid<br />
Benzene<br />
None<br />
Benzene<br />
Benzene<br />
None<br />
_<br />
None<br />
Ether<br />
Benzene<br />
None<br />
_<br />
Dioxane<br />
Benzene<br />
Reaction<br />
Temperature<br />
and Time<br />
131° (432 hr.) f<br />
Room temp. (12<br />
hr.)<br />
40° (24 hr.)<br />
40° (12 hr.)<br />
25° (6 hr.)<br />
50° (6 hr.)<br />
_.<br />
Room temp.<br />
Room temp. (4<br />
days)<br />
140° (20 hr.)<br />
—<br />
_<br />
Reflux (48 hr.)<br />
Fuse<br />
Reflux (48 hr.)<br />
Reflux (22 hr.)<br />
Reflux (21 hr.)<br />
Room temp.<br />
Reflux (96 hr.);<br />
92° (72 hr.)<br />
Reflux (106 hr,)<br />
Reflux (4 days)<br />
190-205° (72 hr,)<br />
160° (26 hr.)<br />
100° (5 hr.)<br />
100° (4 hr.)<br />
170-180° (3 days)<br />
Elevated temps.<br />
160-170°<br />
Reflux (0.5 hr.)<br />
Reflux (5 hr.)<br />
150-180°<br />
—<br />
170-180° (12 hr.)<br />
170-180° (12 hr.)<br />
Yield<br />
%<br />
76<br />
Quant.<br />
Quant.<br />
Quant.<br />
0<br />
—-<br />
—<br />
90<br />
—<br />
70 §<br />
—<br />
96<br />
49$<br />
59 4-<br />
—<br />
80<br />
57 t<br />
64|<br />
21<br />
50<br />
—<br />
—<br />
87.5<br />
0<br />
Quant.<br />
__<br />
_ —<br />
—<br />
* References 324-434 are listed on pp. 57-59.<br />
t Gaseous butadiene was passed into the heated toluene solution of the nitrile for 432 hours.<br />
t Adduct aromatized under these conditions.<br />
§ Product is a mixture of 1-methyl- and 2-methyl-6-methoxyhexahydrophenanthrene-l, 2-dicarboxylio<br />
anhydride.<br />
—<br />
Ref.*<br />
419<br />
320<br />
320<br />
320<br />
320<br />
320<br />
420<br />
5<br />
223<br />
354<br />
221<br />
421<br />
128 6<br />
236<br />
128 a<br />
128"<br />
128"<br />
5<br />
128 tt<br />
128 a<br />
128 a<br />
158<br />
419<br />
275<br />
121<br />
419<br />
415<br />
422<br />
7<br />
7<br />
236<br />
185<br />
157<br />
157
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