The electrophilic addition to an alkene with an electrophile has been widely studied and applied in organic synthesis.The organic chemistry textbook describes the classical reaction between an alkene and an iodine ele...The electrophilic addition to an alkene with an electrophile has been widely studied and applied in organic synthesis.The organic chemistry textbook describes the classical reaction between an alkene and an iodine electrophile(such as elemental iodine and N-iodosuccinimide(NIS))as a typical ionic reaction,in which an iodonium ion is formed and then attacked by a nucleophile.However,in this article,we report a new and unusual reaction mode between an alkene and NIS;that is,a single electron transfer(SET)process occurs between these two reactants by forming an electron-donor acceptor complex.Not only does this unusual single electron transfer reaction between an alkene and NIS add fundamentally important knowledge to organic chemistry,it also provides a valuable synthetic method as the new SET reaction mode with opposite regioselectivity as compared with the traditional ionic mode.展开更多
The Prins reaction between most olefins and formaldehyde shows non-stereospecificity and region selectivity. All the additions of halostyrene, cyclopentene and other olefms are conducted through open ion mechanism. Ho...The Prins reaction between most olefins and formaldehyde shows non-stereospecificity and region selectivity. All the additions of halostyrene, cyclopentene and other olefms are conducted through open ion mechanism. However, the Prins reaction of cyclohexene with water or acetic acid as solvent gives the trans-product stereospecifically with excellent yield. It is considered that the Prins reaction of cyclohexene different from the addition of other展开更多
基金supported by National Key Research and Development Program of China(2021YFF0701700)the National Natural Science Foundationof China(22271299 and 22261132514).
文摘The electrophilic addition to an alkene with an electrophile has been widely studied and applied in organic synthesis.The organic chemistry textbook describes the classical reaction between an alkene and an iodine electrophile(such as elemental iodine and N-iodosuccinimide(NIS))as a typical ionic reaction,in which an iodonium ion is formed and then attacked by a nucleophile.However,in this article,we report a new and unusual reaction mode between an alkene and NIS;that is,a single electron transfer(SET)process occurs between these two reactants by forming an electron-donor acceptor complex.Not only does this unusual single electron transfer reaction between an alkene and NIS add fundamentally important knowledge to organic chemistry,it also provides a valuable synthetic method as the new SET reaction mode with opposite regioselectivity as compared with the traditional ionic mode.
基金The note is a related work of the research subiects supported by the National Natural Science Foundation of China
文摘The Prins reaction between most olefins and formaldehyde shows non-stereospecificity and region selectivity. All the additions of halostyrene, cyclopentene and other olefms are conducted through open ion mechanism. However, the Prins reaction of cyclohexene with water or acetic acid as solvent gives the trans-product stereospecifically with excellent yield. It is considered that the Prins reaction of cyclohexene different from the addition of other
