3-Isopropylidene-2,2-dimethyloxirane (Tetramethylallene Oxide)†‡
Dr. H. M. R. Hoffmann,
Dr. H. M. R. Hoffmann
William Ramsay and Ralph Forster Laboratories, University College, Gower Street, London, W. C. 1 (England)
Search for more papers by this author R. H. Smithers,
Corresponding Author
R. H. Smithers
William Ramsay and Ralph Forster Laboratories, University College, Gower Street, London, W. C. 1 (England)
William Ramsay and Ralph Forster Laboratories, University College, Gower Street, London, W. C. 1 (England)
Search for more papers by this author
Dr. H. M. R. Hoffmann,
Dr. H. M. R. Hoffmann
William Ramsay and Ralph Forster Laboratories, University College, Gower Street, London, W. C. 1 (England)
Search for more papers by this author R. H. Smithers,
Corresponding Author
R. H. Smithers
William Ramsay and Ralph Forster Laboratories, University College, Gower Street, London, W. C. 1 (England)
William Ramsay and Ralph Forster Laboratories, University College, Gower Street, London, W. C. 1 (England)
Search for more papers by this author
First published: January 1970
No abstract is available for this article.
- 1
Allene Oxides, Part 1.
- 2
Work supported by the Science Research Council (London) and the Petroleum Research Fund, administered by the American Chemical Society.
- 3
H. M. R. Hoffmann,
Brit. Pat. 1155535 (February 26, 1968);
French Pat. 1555424 (March 11, 1968);
Germ. Pat. Appl. D 55520 IVb/120 (March 8, 1968);
see also
H. M. R. Hoffmann,
D. R. Joy, and
A. K. Suter,
J. chem. Soc. (London)
B 1968, 57;
H. M. R. Hoffmann and
D. R. Joy,
J. chem. Soc. (London)
B 1968, 1182;
H. M. R. Hoffmann and
N. F. Janes,
J. chem. Soc. (London)
C 1969, 1456.
- 4
R. G. Doerr and
P. S. Skell,
J. Amer. chem. Soc.
89, 4684
(1967).
- 5
Tetramethylallene oxide has previously been implicated as an intermediate in the epoxidation of tetramethylallene with peracetic acid, but was found to be too unstable for isolation under these conditions [6a]; epoxidation of 1,3-di-tert-butylallene yields the remarkably stable 1,3-di-tert-butylallene oxide [6b, 9], which apart from (3) is the only other allene oxide so far isolated.
- 6(a)
J. K. Crandall and
W. H. Machleder,
J. Amer. chem. Soc.
90, 7292
(1968);
see also
J. K. Crandall and
W. H. Machleder,
J. Amer. chem. Soc.
90, 7347
(1968);
J. K. Crandall,
W. H. Machleder,
M. J. Thomas,
J. Amer. chem. Soc.
90, 7346
(1968);
(b)
R. L. Camp and
F. D. Greene,
J. Amer. chem. Soc.
90, 7349
(1968);
see also
R. C. Cookson and
M. J. Nye,
J. Chem. Soc. (London)
1965, 2009.
- 7See
N. J. Turro and
W. B. Hammond,
Tetrahedron
24, 6017
(1968).
- 8
D. P. Wyman and
P. R. Kaufman,
J. org. Chemistry
29, 1956
(1964);
we find that the doublet appears at τ = 8.94 rather than at τ = 8.34 as reported by these authors.
- 9
H. O. House and
G. A. Frank,
J. org. Chemistry
30, 2948
(1965).
