28305-83-1Relevant articles and documents
Synthesis, Characterization, and Chemistry of Bridgehead-Functionalized Bicyclooctanes: Reactions at Neopentyl Sites
Kumar, Kanta,Wang, Shin Shin,Sukenik, Chaim N.
, p. 665 - 670 (1984)
This paper reports the synthesis and characterization of a series of 15 new, symmetric, 1,4-disubstituted bicyclooctyl derivatives.Beyond detailing their syntheses and spectral properties, it describes the scope of synthetic transformations that ca
Competitive C-O Cleavage, S-O Cleavage, and Electron Transfer in the LiAlH4 Reduction of Hindered Disulfonates
Wang, Shin Shin,Sukenik, Chaim N.
, p. 653 - 656 (2007/10/02)
The reaction of heterogeneous slurries of LiAlH4 with several alkanesulfonate substrates is reported.The reducible functional group(s) in each of the substrates is attached to the 1 and/or 4 position of a bicyclooctyl skeleton.The ratio of S-O to C-O bond cleavage reflects a strong transannular electronic effect and is shown to vary with changes in solvent.A new reaction leading to carbon-carbon bond cleavage is also demonstrated, and the competition among these three pathways is shown to be related to both solvent composition and to the heterogeneity of the reaction.The powerful effect of even small amounts of HMPA in THF is delineated and a possible electron-transfer mechanism is presented to account for the carbon-carbon bond cleavage product.