Organic Reactions Volume 4 - Sciencemadness Dot Org

Addends
Vinyl formate
Acecyclone
Cyclopentadiene
Vinyl phenyl ether
Acecyclone
Vinyl p-tolyl ihioeiher
Cyclopentadiene
TABLE VIII—Continued
DIELS-ALDEB ADDITIONS WITH ALLYL, VINYL, AND RELATED COMPOUNDS
Products
l,4-Diphenyl-2,3-(l}8-naphthylene)benzene
l,4-Diplienyl-2,3-(l,8-naphthylene)benzene
^-CH3C6H4S (T^
Ratio of
Diene
to Dienophile
—
0.26
1.0
Solvent
Benzene
Xone
Benzene
None
Temperature,
0 C
180-200t.
180-20Ot.
180-190t,
* References 69-116 are listed on pp. 172-173.
1 The dienophile used was a 30% aqueous solution of allyl alcohol.
2 The structure of the adduct is not definitely established.
s A trace of hydroquinone was added to the reaction mixture.
4 No rearrangement of allyl cyanide to crotononitrile occurs during the addition. The same holds true for the acid.
5 Allyl iodide is sensitive to higher temperatures.
6 The reaction product when hydrogenated and hydrolyzed was characterized as cyclohexanol.
* The melting point of the phenylurethane.
8 The adduct could not be isolated in a pure state.
9 The endo-carbonyl group is lost under these experimental conditions.
10 Two hydrogen atoms and the endo-c&vhonyl group were lost under these experimental conditions.
Time,
hours
16
12
15
B.P. or
M.P.
160-161
160-161
175-178/
11 mm.
Yield,
%
77
40-45
66.5
52
References
*
102
39
102
36
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