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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44 ORGANIC REACTIONS<br />
Butadiene<br />
Butadiene<br />
Butadiene<br />
Butadiene<br />
TABLE III<br />
ADDTJCTS FROM MALBIC ANHYDRIDE WITH ACYCLIC COMPOUNDS<br />
Diene<br />
tfrans-l,3-Pentadiene(frans-piperylene)<br />
tfrans-Piperylene<br />
Piperylene<br />
2-M cthy 1-1 ,3-butadiene (isoprene)<br />
Isoprene<br />
Isoprene<br />
1,3-Hexadiene<br />
2,4-Hexadiene<br />
2,4-Hexadicne<br />
2,4-Hexadiene<br />
2,4-Hexadiene<br />
2-Methyl-l,3-pentadiene<br />
2-Methyl-l,3-pentadiene<br />
2~Methyl-l,3-pontadiene<br />
2-Methyl-l,3-pentadieno<br />
3-Methyl-l,3~pentadiene<br />
4-Methyl-l,3-pentadicne<br />
2,3-Dimethyl-l,3-butadiene<br />
2,3-Dimethyl-l,3-butadiene<br />
2,3-Dimethyl-l,3-butadiene<br />
2,3-Dimethyl-l ,3-butadiene<br />
2,3~Dimethyl-l,3-butadiene<br />
2,4-Heptadiene<br />
5-M ethyl-1,3-hexadiene<br />
3-Methyl-2,4-hexadicne<br />
2,4-Dimethyl-l ,3»pentadicne<br />
2,4-Dimothyl-l,3-pentadiene<br />
4-Ethyl-l,3-hexadiene<br />
2-Cyclopropyl-l,3-butadicne<br />
2,6-Dimethyl-3,5-octadiene<br />
7-Mcthyl-3-methylene-l,6-octadienc<br />
(myrcene)<br />
Myrcene<br />
Myrcene<br />
5-Methyl-4~isopropyl-l,3-hexadieno<br />
1-Phenyl~l,3~butadiene<br />
l-Phenyl-l,3-butadiene<br />
1-Phenyl-l ,3-pentadiene<br />
4-Phenyl-l,3-pentadiene<br />
l-(3 ',4'-MethylenedioxyphenyD-<br />
1,3-butadiene |<br />
2-Methyl-l-phenyl-l,3-butadiene<br />
6-Pheny 1-1,3-hexadiene<br />
4-p-Tolyl-l,3-pentadiene<br />
l-(3',4'-Dimethoxyphenyl)-l,3-butadiene<br />
t<br />
MoIeB<br />
Anhydride<br />
per Mole<br />
Diene<br />
0.88-1.1<br />
1<br />
0.86<br />
—<br />
1<br />
1.2<br />
_.<br />
—<br />
1<br />
1<br />
—<br />
1<br />
—<br />
1<br />
1<br />
1<br />
1<br />
1<br />
1<br />
—<br />
1<br />
—<br />
1<br />
I<br />
1<br />
—<br />
__<br />
_<br />
—<br />
1<br />
1<br />
1<br />
—<br />
1<br />
1<br />
1<br />
0.66<br />
2<br />
1<br />
1<br />
0.5<br />
1.5<br />
Solvent<br />
Benzene<br />
Benzene<br />
Benzene<br />
Benzene<br />
Benzene<br />
None<br />
Benzene<br />
Benzene<br />
Benzene<br />
Benzene<br />
—<br />
Benzene<br />
Benzene<br />
—<br />
Benzene<br />
Benzene<br />
Dioxano<br />
Benzeno<br />
Benzene<br />
Benzene<br />
—<br />
Benzene<br />
Benzene<br />
Dry benzone<br />
Benzeno<br />
Water<br />
(omulsion)<br />
—<br />
Benzene<br />
__<br />
—<br />
Benzene<br />
—<br />
Benzene<br />
—<br />
None<br />
None<br />
None<br />
_<br />
None<br />
—<br />
None<br />
Benzene<br />
Xylene<br />
Dry benzene<br />
Xylene<br />
Benzene<br />
Xylene<br />
Reaction Temperature<br />
and Time<br />
Room temp. (12 hr.); 100°<br />
(5 hr.)<br />
Room temp. (24 hr.)<br />
Room temp. (12 hr.); 100°<br />
(5 hr.)<br />
Room temp. (2 days); 100°<br />
(8hr.)<br />
0° (5 days)<br />
100° (2.5 hr.)<br />
Room temp.<br />
Room temp.<br />
Gentle heat<br />
0° (12 hr.); 100° (several<br />
hours)<br />
—<br />
Room temp. (24 hr.)<br />
—<br />
— 0° (12 hr.); 100° (several<br />
hours)<br />
Room temp.<br />
4°<br />
Room temp. (1 week)<br />
0° (12 hr.); 100° (several<br />
hours)<br />
0° (12 hr.); 100° (several<br />
hours)<br />
— 0° (12 hr.); 100 (several<br />
hours)<br />
Room temp.<br />
Room temp. (24 hr.)<br />
Heated<br />
40° (12 hr.)<br />
—<br />
Room temp. (> 1 week)<br />
__<br />
—<br />
Room temp. (2-3 days)<br />
__<br />
—<br />
Warm<br />
Warm gently<br />
Fuse<br />
__<br />
Warm<br />
Heat<br />
Warm<br />
100-105° (2 hr.)<br />
Reflux (3 hr.)<br />
100° (6 hr.)<br />
Room temp. (4 days)<br />
105-110° (2 hr.)<br />
Reflux (7.5 hr.)<br />
Yield<br />
%<br />
Quant.<br />
Quant.<br />
90<br />
—<br />
95<br />
97<br />
—<br />
—<br />
Quant.<br />
—<br />
—,<br />
Quant.<br />
—<br />
77<br />
—<br />
Quant.<br />
96<br />
—<br />
Quant.<br />
—<br />
Quant.<br />
—<br />
Good<br />
—<br />
Quant.<br />
Quant.<br />
—<br />
6<br />
Quant.<br />
—<br />
20<br />
14<br />
55<br />
Ref.*<br />
5<br />
148<br />
323<br />
324<br />
131<br />
140<br />
6<br />
6<br />
324<br />
131<br />
135<br />
6<br />
135<br />
325<br />
131<br />
6<br />
132<br />
134<br />
131<br />
131<br />
137<br />
131<br />
6<br />
148<br />
324<br />
320<br />
135<br />
134<br />
135<br />
326<br />
6<br />
137<br />
327<br />
19<br />
6,328<br />
* References 324-434 are listed on pp. 57-59.<br />
f Piperonylallylcarbinol which was dehydrated under the reaction conditions was employed.<br />
1 3,4-Dimethoxyphenylallylcarbinol which was dehydratod under the reaction conditions was<br />
employod.<br />
329<br />
330<br />
137<br />
151<br />
331<br />
151<br />
18<br />
333<br />
331<br />
136<br />
18<br />
333
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