Conclusions
We have systematically studied the mass spectra of the halides of the bicyclo[n.1.O]alkane series (n=4–6), showing the principal mode for fragmentation of these compounds to involve opening of the cyclopropane ring with subsequent elimination of the ring fragments.
Similar content being viewed by others
Literature cited
É. S. Agavelyan, Dissertation, Moscow (1972), p. 73a.
H. Weitkamp, U. Hasserodt, and F. Korte, Chem. Ber.,95, 2280 (1962); P. Natalis and J. Laune, Bull. Soc. Chim. Belg.,73, 944 (1964); L. Friedman, J. J. Leventhal, and T. F. Moran, J. Am. Chem. Soc.,88, 5050 (1966); W. G. Dauben, J. H. Smith, and J. Saltiel, J. Org. Chem.,34, 261 (1969); R. Bloch, J. M. Dedien, and J. M. Conia, Bull. Soc. Chim. France, 1875 (1970); W. R. Moore, S. E. Krikorian, and J.E. La-Prade, J. Org. Chem.,28, 1040 (1963); E. K. Fields and S. Meyerson, J. Org. Chem.,28, 1915 (1963); C. Lifshitz and F. A. Long, J. Phys. Chem.,69, 3741 (1965); R. R. Pottie, A. G. Harrison, and F.P.Lossing, J. Am. Chem. Soc.,83, 3204 (1961); F. H. Field, J. Chem. Phys.,20, 1734 (1952); G. Salmona, J.-P. Galy, and E.-J. Vineet, Compt. Rend., C273, 685 (1971).
M. L. Deem and J. Roboz, Org. Mass Spectrom.,3, 155 (1970).
K. A. Chochua, O. S. Chizhov, Yu. S. Shabarov, and N. A. Kazbulatova, Zh. Org. Khim.,7, 1024 (1971); K. A. Chochua, O. S. Chizhov, and Yu. S, Shabarov, Zh. Org. Khim.,7, 2028 (1971).
K. A. Chochaa, O. S. Chizhov, and Yu. S. Shabarov, Zh. Org. Khim.,8, 970 (1972).
K. A. Chochua, Dissertation, Moscow (1972).
R. E. Winters and J. H. Collins, Org. Mass Spectrom.,2, 299 (1969).
J. R. Dias and C. Djerassi, Org. Mass Spectrom.,7, 753 (1973).
R. E. Winters and J. H. Collins, J. Am. Chem. Soc.,90, 1235 (1968).
A. J. Dale, W. D. Weringa, and D. H. Williams, Org. Mass Spectrom.,6, 501 (1972).
S. Pignatora, A. Cassuto, and F. P. Lossing, J. Am. Chem. Soc.,89, 3693 (1967).
O. M. Nefedov and É. S. Agavelyan, Izv. Akad. Nauk SSSR, Ser. Khim., 2045 (1973).
O. M. Nefedov and F. S. Agavelyan, Izv. Akad. Nauk SSSR, Ser. Khim., 838 (1974).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 91–97, January, 1977.
See [1] also.
The authors wish to thank Dr. Tomash (Research Laboratory for Chemical Structure of the Academy of Sciences of the Peoples Republic of Hungary) for having shown the identity of the mass spectra of the isomers of (VI). They would also like to thank O. S. Chizhov for his interest in this work, and B. M. Zolotarev for a valuable discussion.
Rights and permissions
About this article
Cite this article
Agavelyan, É.S., Mal'tsev, A.K. & Nefedov, O.M. Mass spectra of the bicyclo[n.1.0]alkanes and their halogen derivatives. Russ Chem Bull 26, 77–83 (1977). https://doi.org/10.1007/BF00921497
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00921497