Generation of mono- and bis-dioxiranes from 2,3-butanedione.
نویسندگان
چکیده
Biacetyl reacts with oxone to give bis-dioxirane [3,3'-dimethyl-3,3'-bidioxirane, 3B] and mono-dioxirane [1-(3-methyl-dioxiran-3-yl)ethanone, 3A)]. Bis-dioxirane 3B is formed when two oxygens are incorporated into biacetyl, while mono-dioxirane 3A incorporated only one. A greater stability is observed in 3B compared to 3A, which is attributed to an alpha-dioxiranyl (anomeric) effect in the former. In contrast, 3A suffers from a destabilizing pi-electron withdrawing effect from the adjacent carbonyl group.
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ورودعنوان ژورنال:
- The Journal of organic chemistry
دوره 71 15 شماره
صفحات -
تاریخ انتشار 2006