Story synthesis

When cycloaikylidine peroxides (e.g., 59) are heated in an inert solvent (e.g., decane), extrusion of CO2 takes place the products are the cycloalkane containing three carbon atoms less than the starting peroxide and the lactone containing two carbon atoms less" (the Story synthesis). The two products are formed in comparable yields, usually 15-25% each. Although the yields are low, the reaction is... 

Story Denson Bishop Clark Farinc 1. Am. Chem. Soc. 1968, 90. 817 Sanderson Story Paul J. Org. Chem. 1975, 40. 691 Sanderson Paul Story Synthesis 1975, 275. 

Treatment of cyclic ketones (Figure 3.51) under acid conditions can give rise to dimeric cycloalkylidene peroxides, which on thermolysis give lactones and CO2 (the Story synthesis).242... 

H202 added slowly at 20-30° to a mixture of cyclohexanone and 10%-perchloric in glacial acetic acid, after stirring 15-20 min. at 40-45° more glacial acetic acid added, and the soln. warmed 0.5-1 hr. at 55-60° -> crude tricyclo-hexylidene triperoxide. Y 83%. F. e. s. J. R. Sanderson, K. Paul, and P. R. Story, Synthesis 1975, 275 mixed cyclic ketone peroxides cf. ibid. 1975, 388 J. Org. Chem. 41, 1283 (1976) cyclic ketone diperoxides in acetonitrile-methylene chloride in the presence of methanesulfonic acid s. ibid. 40, 2239 (1975) tricyclohexylidene triperoxide s. a. M. J. C. Harding and D. M. Whalen, Ind. Eng. Chem., Prod. Res. Dev. 14, 232 (1975). 

An early success story in the field of catalytic asymmetric synthesis is the Monsanto Process for the commercial synthesis of l-DOPA (4) (see Scheme 1), a rare amino acid that is effective in the treatment of Parkinson s disease.57 The Monsanto Process, the first commercialized catalytic asymmetric synthesis employing a chiral transition metal complex, was introduced by W. S. Knowles and coworkers and has been in operation since 1974. This large-scale process for the synthesis of l-DOPA (4) is based on catalytic asymmetric hydrogenation, and its development can be... 

The aim of this volume is to convince the reader that metal carbene complexes have made their way from organometallic curiosities to valuable - and in part unique - reagents for application in synthesis and catalysis. But it is for sure that this development over 4 decades is not the end of the story there is both a need and considerable potential for functional organometallics such as metal carbon multiple bond species which further offer exciting perspectives in selective synthesis and catalysis as well as in reactions applied to natural products and complex molecules required for chemical architectures and material science. 

The story of the heavy analogs of 6jt-electron cyclopentadienyl anions has culminated in the latest synthesis of a compound containing three heavier group 14 elements (two Si and one Ge) in the ring. This aifionic species 69 Li+ was prepared by the reduction of the disilagermacyclopentadiene precursor 70 with potassium graphite KCg followed by the exchange of countercation from K+ to Li+ by treatment with LiBr (Scheme 2.66). ... 

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