Lithium aluminum hydride reduction of 1-aryl-3-halopropenes, 1-aryl-3-halobutenes, and (9-anthryl)arylmethyl halides. Nucleophilic substitution vs. single electron transfer

1985 ◽  
Vol 50 (11) ◽  
pp. 1797-1802 ◽  
Author(s):  
Tomoatsu Hirabe ◽  
Masato Takagi ◽  
Kiyoshige Muraoka ◽  
Masatomo Nojima ◽  
Shigekazu Kusabayashi
Keyword(s):  
Electron Transfer ◽  
Nucleophilic Substitution ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Single Electron ◽  
Lithium Aluminum ◽  
Single Electron Transfer ◽  
Hydride Reduction

Rearrangements Involving the Tricyclo[3.1.1.03,6]heptyl and Tricyclo[3.2.1.03,6]octyl Systems. Single-Electron Transfer in the Reduction of a Bridgehead Tosylate With Lithium Aluminum Hydride

1992 ◽  
Vol 45 (8) ◽  
pp. 1205 ◽  
Author(s):  
EW Della ◽  
WK Janowski ◽  
PE Pigou
Keyword(s):  
Electron Transfer ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Single Electron ◽  
Lithium Aluminum ◽  
Single Electron Transfer ◽  
Lithium Aluminium Hydride ◽  
Alkoxy Radicals ◽  
Lithium Aluminium

The attempted conversion of tricyclo [3.1.1.03,6]heptane-6-methanol (9) into the corresponding tosylate (7) leads instead to a rearranged isomer tricyclo [3.2.1.03,6]oct-6-yl tosylate (10). Treatment of 10 with lithium aluminium hydride affords a mixture of the parent alcohol tricyclo[3.2.1.03,6]octan-6-ol (15) and endo-bicyclo[3.2.l]octan-6-ol. The available evidence suggests that the latter arises by a process which appears to be mediated by alkoxy radicals rather than anions.

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