By Zvi Rappoport, Peter J. Stang
The 1st name during this sector in lots of years, this name brings jointly the entire components of curiosity in natural reactions related to carbocations in a single convenient quantity. It covers new components corresponding to nuclear decay new release, man made purposes and NMR observations. additionally incorporated is vast and certain insurance of theoretical and fuel part information.
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Extra info for Dicoordinated carbocations
Sample text
A second report3 stated that the potassium salts of cis- and trans-b chlorocinnamic acid (1b) and (2b), respectively, were decarboxylated in water at 120°C, the former faster than the latter. These reports clearly indicated that vinyl halides do react in water when suitably substituted. A detailed investigation of these and related reactions was therefore undertaken4. The study confirmed that salts of cis-b-bromo and cis-b-chlorocinnamic acids (1a) and (1b), respectively, led to phenylacetylene (3) when heated in aqueous solution.
The application of these more recent, modern techniques to vinyl cations along with the more traditional methods of solvolysis and electrophilic addition to alkynes and allenes has provided new and interesting insights into the nature and reaction chemistry of dicoordinated carbocations. This new understanding in turn allowed the synthetic organic chemist to use vinyl cations in both synthetic transformations and natural product synthesis. Hence, it was time to summarize all these advances and new developments in dicoordinated carbocations and we hope that the present monograph fulfills this purpose.
The reaction products of the bromodienes 24 to 29 confirmed the presence of two electrophilic centers in the mesomeric cation 30. Thus, in 80% ethanol the 4-ethoxyallenes 34 were the main products along with varying amounts of the alkenynes 32 and the a, b-unsaturated ketones 33, the latter being formed via the enol 35. In the case studies described so far the intermediate vinyl cations were assumed to possess a linear sp configuration 36, where R represents an aryl group or a second double bond.