20530-06-7Relevant academic research and scientific papers
Free-radical based cycloalkanol synthesis and annulation from thioacetal precursors
Yadav, Veejendra,Fallis, Alex G.
, p. 779 - 789 (2007/10/02)
A general procedure for the synthesis of diverse cyclopentanols via free-radical cyclization of unsaturated 1,3-oxathiolanes and 1,3-oxathiolan-5-ones is described.The scope of these reactions, including preliminary rate studies that indicate that the 1,3-oxathiolan-5-ones cyclize at a useful rate (1.4*106 M-1s-1 at 80 deg C), has been examined.This permits the rapid assembly, by intramolecular annulation, of various additional ring systems, including bicyclooctanols, bicyclononanols, and bicyclooctanols for use in total synthesis. Key words: radical cyclization, oxathiolanes, oxathiolanones.
Rearrangements of 6-Bicyclooctyl Cations
Brandt, Sigrid,Kirmse, Wolfgang,Moench, Dietmar,Wroblowsky, Heinz-Juergen
, p. 887 - 893 (2007/10/02)
6-Bicyclooctyl cations were generated by nitrous acid deaminations of the amines 12, 14 and by acetolyses of the tosylates 9, 20.The major products are bicyclooctan-exo-6-ol (17), bicyclooctan-exo-2-ol (18), and bicyclooctan-2-
BRIDGING STRAIN IN BICYCLIC CARBOCATIONS
Grob, Cyril A,Zutter, Ulrich
, p. 2849 - 2852 (2007/10/02)
The solvolysis rates and products of 6-exo- and 6-endo-bicyclooctyl toluenesulfonate confirm that differential bridging strain is a major factor in determining the reactivity of epimeric bicyclic sulfonates.
