85202-08-0Relevant articles and documents
DEOXYGENATION OF ALDEHYDES AND KETONES; A NEW GENERAL REACTION OF DIBROMOCARBENE AND DIBROMOCARBONYL YLIDES
Huan, Zhenwei,Landgrebe, John A.,Peterson, Kimberly
, p. 2829 - 2832 (1983)
The treatment of a variety of aldehydes and ketones with phenyl(tribromomethyl)mercury results in the production of carbon monoxide from the deoxygenation of the carbonyl group by dibromocarbene.
Dibromocarbonyl Ylides. Deoxygenation of Aldehydes and Ketones by Dibromocarbene
Huan, Zhenwei,Landgrebe, John A.,Peterson, Kimberly
, p. 4519 - 4523 (2007/10/02)
The reaction of phenyl(tribromomethyl)mercury (4) with benzaldehyde-α-13C results in benzal-α-13C bromide and CO.The generality of this deoxygenation was shown by treatment of other aldehydes and ketones with mercurial 4 (1.8:1, benzene, 80 deg C, 4 h): , Ph (46), Et (35), i-Pr (39), t-Bu (19); Ph, Ph (6), Ph, Me (15), Me, Me (16), Et, n-Bu (19), Me, c-C3H5 (20), c-C3H5, c-C3H5 (20), cyclohexanone (38), cyclopentanone (19), norcamphor (46).Additional products in selected cases include (for acetophenone) α-bromostyrene, (for cyclohexanone) 1-bromocyclohexene and 1,1-dibromocyclohexane, (for norcamphor) 2,2-dibromonorbornane, 1,2-dibromonorbornane, 2-bromo-2-norbornene and 1-bromonorbornene, and (for pivaldehyde) 1,1-dibromo-2,2-dimethylpropane.The yields of CO from the treatment of a series of benzaldehydes with mercurial 4 (1.8:1 benzene, 80 deg C, 20 h) are given in parentheses: ArCHO (percent CO), 4-MeO (81), 4-Me (61), 3-Me (55), H (50), 4-F (46), 3-MeO (58), 4-Cl (46), 4-Br (47), 3-Cl (34), 3,4-Cl2 (27).A Hammett-type correlation of log (yield)/(yield)0 vs. ? gave ρ = -0.50 (r = 0.94).
