Propeilanes- XX
1823
30 g maleic anhydride) of the desired product was ob-
tained, m.p. 167-167.5° (EtOH). Lit) ° m.p. 168-169°.
IR (KBr): 1838, 1770 cm-1 (anhydride CO).
Attempted synthesis of5~ A mixture of distilled styrene
(0-62g), freshly crystallized N-methylmaleimide (0.74 g),
hydroquinone (10mg) and dry toluene (10ml) was
for comparison, n Finally, the dimer 2 (140 mg; 15%)
was identical to an authentic specimen. 2c
REFERENCES
IL. T. Scott and M. Jones, Jr., Chem. Revs., 72, 181
(1972)
heated in
170-180° for 5-5hr. The tube contained a clear soln
which deposited yellowish solid after cooling. The
a sealed tube (25 cm long, 8 mm diam) at
2aj. Airman, E. Babad, D. Ginsburg and M. B. Rubin,
Israel J. Chem. 7, 435 (1969); ~J. Altman and D.
Ginshurg, Tetrahedron 27, 93 (1971); cO. Sciacovelli,
W. yon Philipsborn, C. Amith and D. Ginsburg, Ibid.
26, 4589 (1970); ~ . Amith, B. North, unpublished
results; %V. yon Philipsborn, J. Altman, E. Babad, J. J.
Bloomfield, D. Ginsburg and M. B. Rubin, Heir. Chim.
Acta 53, 725 (1970)
~V. Grimme H.J. Riebel and E. Vogel, Angew. Chem.
Int. Ed. Engl. 7, 823 (1968); bM. Jones, Jr. and B. Fair-
less, Tetrahedron Letters 4881 (1968); OR. T. Seidner,
N. Nakatsuka and S. Masamune, Canad. J. Chem.
48, 187 (1970); c f a W . E. Doering and J. W. Rosenthal,
J . A m . Chem. Soc. 88, 2078 (1966); ldem., Tetrahedron
Letters 349 (1967)
a
supernatant liquid was removed and the yellow solid
was triturated with ether. The colorless residue (260 nag)
was crystallized from MeOH, affording a product, m.p.
188-190° (13.5%). This was the bis-adduct.* (Found: C,
66.44; H, 5.50; N, 8.64. C~sHlsN,O4 requires: C, 66.24;
H, 5.56; N, 8-58%); IR(KBr): 1775, 1700 cm-~ (imide
CO); NMR (acetone-de): T 2-10 (t, 1 ArH); 2.72 (m, 3
ArH); 5-72 (d, 1 benzylic H); 6.60 (m, 3 H); 7.07, 7.10 (2s,
6 NC_Ha); 7-70-7'00 (m, 4 H); M.S., M ÷, 326; 268,254,
214. The NMR spectrum of the anhydride exhibited
bands in CDCI3 (T-60 Varian): r 1.10(m, 1 H); 1.58-2.21
(m, 5H). For 5:1-10 (m, 1 H); 1.65-2.40 (m, 5H); 6.80
(s, NCH~).
4C. D. Nenitzescu, M. Avram and E. Marica, Chem. Ber.
90, 1857 (1957)
5H. E. Zimmermann and G. L. Grunewald, J. Am. Chem.
Soc. 86, 1434 (1964)
This was followed by
3 (120mg; 13%), m.p. 133 °
identical by admixture with an authentic specimen and
by IR and NMR spectra. Compound 4 (20 nag; 2%), m.p.
205° was similarly identical to an authentic specimen. 2a
Next to be eluted was 7 (75 rag; 8-5%; total yield 103
mg; 11%), m.p. 239-240~. It was identical to the authentic
specimen prepared for comparison)t Compound 6 (10
mg; 1%), m.p. 180-181 ° (EtOH) was assigned its struc-
ture on the basis of M +, role 213; IR(KBr): 1765, 1695,
1660, 1600 era-l; and NMR spectrum (CDCI3): ~" 2"24
(d), 2.65 (s), total 5 H; 6.99 (s, NC_H3); 6-55-7.21 (m, 2
benzylic, 1 allylic H). Compound 8 (20 mg; 2%), m.p.
205° was identical to the authentic specimen prepared
8L. A. Paquette, Ibid. 93, 7110 (1971)
Taj. A. Berson, Accounts Chem. Res. 1, 152 (1968); ~S.
Masamune, S. Takada, N. Nakatsuka, R. Vukov and
E. N. Cain, J, Am. Chem. Soc. 91, 4322 (1969)
8cf L. A. Paquette, M. J. Kukla and J. C. Stowell, Ibid.
94, 4920 (1972)
9.i.H. Brewster and A. M. Fusoo, J. Org. Chem. 28, 501
(1963)
I°K. Alder and R. Schmitz-Josten, Liebigs Ann. 595, 1
(1965)
riD. F. Roswell, V. Paul and E. H. White, J. Am. Chem.
Soc. 92, 4855 (1970)
riG. F. Janbert, Bet. Dtsch. Chem. G es. 28, 360 (1895)
*See previous page.