Journal of the American Chemical Society p. 9386 - 9390 (1992)
Update date:2022-08-16
Topics:
Moss, Robert A.
Balcerzak, Pawel
The fragmentation of (S)-3-(2-butoxy)-3-chlorodiazirine (9) in acetonitrile proceeds via N2 loss to (5)-2-butoxy-chlorocarbene (10) and thence via CO scission to a 2-butyl cation/chloride anion pair (11) that collapses to (5)-2-chlorobutane (12) with ～56% net retention. In 1-butanol, ion pair 11 affords 55% chloride 12 by ion pair return with 82% net retention and 45% of (R)-2-butyl 1-butyl ether (13) by ion pair solvolysis with ～71% net inversion.
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