Summary
-
1.
It has been shown that the reaction of mercurated acetaldehyde with carboxylic acid chlorides results in the formation of the corresponding vinyl esters. In a similar way, bromotris(p-nitrophenyl)methane yieds the corresponding vinyl ether. In these reactions transfer of reaction center along the system of conjugated Hg-C and C=O bonds occurs.
-
2.
It has been shown that the reaction of mercurated acetaldehyde with bromotriphenylmethane results in the formation of 3,3,3-triphenylpropionaldehyde, i.e. C-alkylation occurs, without transfer of reaction center.
-
3.
The previously undescribed vinyl esters of trichloroacetic, phenylacetic, triphenylacetic, phthalimidoacetic, p-nitrobenzoic acids have been prepared.
-
4.
The synthesis and ozonization of 4,4,4-triphenyl-1-butene have been described.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. N. Nesmeyanov and I. F. Lutsenko, Proc. Acad. Sci. USSR, 59, 707 (1948).
A. N. Nesmeyanov, I. F. Lutsenko, and Z. M. Tumanova, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1949, 601.
A. N. Nesmeyanov, Sci. Mem. Moscow State Univ., No. 132, Book 7, p. 16 (1950).
L. Hellerman and R. L. Garner, J. Am. Chem. Soc. 68, 819 (1946).
K. Ziegler, E. Boye, Ann. 458, 252 (1927).
G. N. Lewis, D. Lipkin, T. T. Magel, J. Am. Chem. Soc., 66, 1583 (1944).
J. E. Leffler, J. Am. Chem. Soc., 75, 3598 (1953).
R. H. Wiley, Org. Syntheses 28, 94 (1948).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nesmeyanov, A.N., Perevalova, E.G. Alkylation and acylation of (chloromercuri)acetaldehyde. Russ Chem Bull 3, 873–877 (1954). https://doi.org/10.1007/BF01168170
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01168170