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Polar Substituent Effects in the Bicyclo[1.1.1]pentane Ring System: Acidities of 3-Substituted Bicyclo[1.1.1]pentane-1-carboxylic Acids

โœ Scribed by Adcock, William; Baran, Yakup; Filippi, Antonello; Speranza, Maurizio; Trout, Neil A.


Book ID
121484127
Publisher
American Chemical Society
Year
2005
Tongue
English
Weight
134 KB
Volume
70
Category
Article
ISSN
0022-3263

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Ab initio SCF cafwhtions have been performed on bicycle [ 1.1.1 f pentsne aird on its bridgehead anion and cation. The most striking result ties in the strong interaction between the two bridgehead sites which may be related to the properties of thi!; strained molecuie.

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A series of 3-substituted(X)bicyclo[1.1.1]pent-1-yl fluorides (1) together with a more limited series of 3-substituted(X)bicyclo[1.1.1]pent-1-yl trifluorides (4) were synthesized and their 19 F and 13 C NMR spectra were recorded. Correlation of the 19 F substituent chemical shifts (SCS) of 1 against