Acid-catalyzed cyclization reactions. XI. Competitive amide versus thioamide cyclization. Cyclization of N-allylrhodanine in strong acid media

1974 ◽  
Vol 39 (20) ◽  
pp. 3041-3042 ◽  
Author(s):  
Samuel P. McManus ◽  
Kin Y. Lee
1976 ◽  
Vol 41 (11) ◽  
pp. 1895-1899 ◽  
Author(s):  
Samuel P. McManus ◽  
Richard A. Hearn ◽  
Charles U. Pittman

1974 ◽  
Vol 52 (11) ◽  
pp. 2085-2097 ◽  
Author(s):  
C. R. Jablonski ◽  
T. S. Sorensen

Both the tricarbonyl(1,4-dimethylene-cis, cis, trans, cis-hexa-1,3-dienyl)iron (secondary) and the tricarbonyl(1,4-dimethylene-5-methyl-cis, cis, trans-hexa-1,3-dienyl)iron (tertiary) cations, which cannot convert to a 5h-cis pentadienyl system via a simple bond rotation, can be prepared at low temperature in strong acid media from their related alcohol complexes. The secondary as well as the tertiary ions rearrange to give the thermodynamically more stable tricarbonyl-(1-alkylcyclohexa-1,3-dienyl)iron cation via an acid catalyzed pseudo first order process. The rate of rearrangement of the secondary ion is much faster than that of the tertiary ion indicating a substantial amount of residual positive charge on the exocyclic (β) carbon in the complexed trans-pentadienyl carbonium ions.


2021 ◽  
Vol 510 ◽  
pp. 111687
Author(s):  
Wenhao Yuan ◽  
Wenlai Xie ◽  
Jiaxi Xu

1970 ◽  
Vol 35 (4) ◽  
pp. 1187-1190 ◽  
Author(s):  
Charles U. Pittman ◽  
Samuel P. McManus
Keyword(s):  

Author(s):  
C. Dennis Hall ◽  
Christopher J. Leeding ◽  
Stephen Jones ◽  
Stephen Case-Green ◽  
Ian Sanderson ◽  
...  

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