A new method of reducing the carbonyl group of aryl ketones to a methylene group

Author(s):  
D. N. Kursanov ◽  
Z. N. Parnes ◽  
N. M. Loim
1956 ◽  
Vol 34 (11) ◽  
pp. 1519-1527 ◽  
Author(s):  
L. R. C. Barclay ◽  
David B. MacLean

The hydrogenolysis and hydrolysis of α-cyanobromolycopodine to the secondary tricyclic base, α-des-dihydrolycopodine, is reported. The latter compound was converted to the methiodide in poor yield so that further degradations of the molecule through this derivative were not feasible. Hydride reductions of α-cyanobromolycopodine and some of its derivatives are recorded. The presence of a methylene group adjacent to the carbonyl group in lycopodine has been proved. Evidence is presented which suggests that the carbonyl group and the nitrogen atom are relatively close to one another in the molecule.


1961 ◽  
Vol 14 (1) ◽  
pp. 48
Author(s):  
CS Barnes ◽  
BD Beilby

Doubly bonded methylene groups have been introduced into 7α- and 11β-acetoxylanostanes and the rate of hydrolysis compared with compounds having a hydroxy or carbonyl group at the same position as the methylene group. It was found that methylene groups facilitate hydrolysis of the hindered acetoxy groups in the same way, but not to the same extent, as carbonyl groups. It is concluded that the facilitation in each case results from a conformational disturbance, but that there is some other factor involved in carbonyl facilitation. It was not possible to demonstrate a similar effect resulting from steric crowding of substituents.


1983 ◽  
Vol 48 (11) ◽  
pp. 1939-1940 ◽  
Author(s):  
Tatsuya Shono ◽  
Shigenori Kashimura
Keyword(s):  

1975 ◽  
Vol 53 (4) ◽  
pp. 589-595 ◽  
Author(s):  
S. H. Grover ◽  
J. B. Stothers

The shielding effects of the exo-methylene group on neighboring carbons in several cycloalkanes, methylcyclohexanes, and in the norbornane ring system have been characterized by 13C n. m. r. examination of 28 compounds. The results are compared with those for the carbonyl group and the utility of these data for structural elucidations is discussed. The more distinctive trends exhibited by the methyl carbons in these systems are compared with those for cyclohexanes, cyclohexanones, norbornanes, and norcamphors.


Author(s):  
Younes Zaoui ◽  
Youssef Ramli ◽  
Jamal Taoufik ◽  
Joel T. Mague ◽  
Mukesh M. Jotani ◽  
...  

The title compound, C16H18N2O3, is constructed about a central oxopyridazinyl ring (r.m.s. deviation = 0.0047 Å), which is connected to an ethylacetate group at the N atom closest to the carbonyl group, and benzyl and methyl groups second furthest and furthest from the carbonyl group, respectively. An approximately orthogonal relationship exists between the oxopyridazinyl ring and the best plane through the ethylacetate group [dihedral angle = 77.48 (3)°]; the latter lies to one side of the central plane [the Nr—Nr—Cm—Cc (r = ring, m = methylene, c = carbonyl) torsion angle being 104.34 (9)°]. In the crystal, both H atoms of the N-bound methylene group form methylene-C—H...O(ring carbonyl) or N(pyridazinyl) interactions, resulting in the formation of a supramolecular tape along the a-axis direction. The tapes are assembled into a three-dimensional architecture by methyl- and phenyl-C—H...O(ring carbonyl) and phenyl-C—H...O(ester carbonyl) interactions. The analysis of the calculated Hirshfeld surface indicates the dominance of H...H contacts to the overall surface (i.e. 52.2%). Reflecting other identified points of contact between molecules noted above, O...H/H...O (23.3%), C...H/H...C (14.7%) and N...H/H...N (6.6%) contacts also make significant contributions to the surface.


Heterocycles ◽  
1981 ◽  
Vol 15 (2) ◽  
pp. 1159 ◽  
Author(s):  
Kin-ya Akiba ◽  
Hiroshi Yamaoka ◽  
Tatsushi Hakucho

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