24268-20-0Relevant academic research and scientific papers
CATALYTIC EXTENDED DOUBLE BOND MIGRATION WITH RETENTION OF CONFIGURATION: A "ZIP-REACTION"
Weissberger, E.,Stockis, A.,Carr, D. D.,Giebfried, J.
, p. 281 - 288 (2007/10/02)
(+) Citronellol was catalytically isomerized by Fe(CO)5 into (+) dihydrocitronellal with partial retention of configuration: the optical yield was 16 +/- 1 percent at 140 deg C.Isolation of partially isomerized intermediates and use of citronellol deuterated at various positions allowed a clear description of the reaction mechanism as a succession of 1,3 hydrogen shifts.The observed partial retention of configuration suggests that full 1,7 isomerization occurs before metal-olefin dissociation occurs even once.
