19550-87-9Relevant articles and documents
Thermal decomposition of meso- and d,l-3,4-diethyl-3,4-dimethyldiazetine N,N′-dioxide
Breton, Gary W.,Nickerson, Justine E.,Greene, Anna M.,Oliver, Lindsey H.
, p. 3005 - 3008 (2007)
Two stereochemically defined diazetine N,N′-dioxides were synthesized. Thermal decomposition at 200 °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.
α-Thio-substituted Ketones as Precursors of Olefins via Oxathiolanes: Benzyl as Protecting Group
Brown, Michael D.,Whitham, Gordon H.
, p. 817 - 822 (2007/10/02)
The feasibility of a regiospecific synthesis of tetrasubsituted olefins starting from protected α-thiol substituted ketones has been demonstrated by three examples.The approach (see Scheme) involves: S-activated alkylation (i), carbonyl addition of an organometallic reagent (ii), deprotection (iii), formation of a 2-phenyloxathiolane (iv), and base-promoted cycloelimination (v).An unsatisfactory feature is the lack of stereochemical control in step (ii).An attempt to telescope steps (iii) and (iv) by sequential Pummerer reaction-cyclisation at the β-benzylthio alcohol stage was unsuccessful.
