Another challenge to the validity of the use of cyclizable probes as evidence for single-electron transfer in nucleophilic aliphatic substitution. The reaction of lithium aluminum hydride with alkyl iodides [Erratum to document cited in CA110(3):23019s]

1989 ◽  
Vol 54 (13) ◽  
pp. 3246-3246
Author(s):  
E. C. Ashby ◽  
Pham Tung ◽  
A. Amrollah Madjdabadi
Keyword(s):  
Electron Transfer ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Single Electron ◽  
Lithium Aluminum ◽  
Single Electron Transfer ◽  
Alkyl Iodides

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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