Thermal Decomposition of <i>meso</i>- and <i>d,l</i>-3,4-Diethyl-3,4-dimethyldiazetine <i>N,N</i>‘-Dioxide
作者:Gary W. Breton、Justine E. Nickerson、Anna M. Greene、Lindsey H. Oliver
DOI:10.1021/ol0710414
日期:2007.8.1
Two stereochemically defined diazetine N,N'-dioxides were synthesized. Thermal decomposition at 200 degrees C resulted in 95% retention of stereochemistry in the alkene product relative to the starting stereochemistry. These results suggest that decomposition occurs via cleavage of the two C-N bonds either simultaneously or in rapid succession.
The reaction of various cyclic and acyclic alkynes with lithium dust (2% sodium) to form vicinal dilithioalkenes has been investigated: Aliphatic alkynes, e.g. 3-hexyne (27a), exclusively afford the corresponding (E)-dilithioalkenes, insoluble solids which are stable at room temperature and allow access to a variety of tetrasubstituted olefins in acceptable yields