Reaction products of primary β-hydroxyamines with carbonyl compounds: XVI) Condensation of Carbonyl Compounds with 4-Hydroxy- and 4- Mercaptobutylamine

1959 ◽  
Vol 78 (5) ◽  
pp. 331-336 ◽  
Author(s):  
Ernst D. Bergmann ◽  
A. Kaluszyner
2000 ◽  
Vol 78 (10) ◽  
pp. 1325-1344
Author(s):  
Wolfgang Kliegel ◽  
Gottfried Lubkowitz ◽  
Jens O Pokriefke ◽  
Steven J Rettig ◽  
James Trotter

Synthesis has been carried out of diarylboron chelates of 2- and 3-hydroxynitrones, of 2- and 3-hydroxyoximes, and of 2-carboxynitrones and a 2-carboxyoxime. The structures have been determined from spectroscopic data and from X-ray analyses of 5d, 9a, 11b, and 19. Crystals (at 180 K) of 5d are monoclinic, a = 10.543(2), b = 19.085(4), c = 10.2667(3) Å, β = 90.4978(7)°, Z = 4, space group P21/c; those of 9a are orthorhombic, a = 10.9913(5), b = 14.9329(7), c = 10.2460(13) Å, Z = 4, space group P212121; those of 11b are monoclinic, a = 11.227(2), b = 9.967(2), c = 17.0537(4) Å, β = 105.4179(5)°, Z = 4, space group P21/n; those of 19 are monoclinic, a = 11.1847(15), b = 13.715(3), c = 11.5559(5) Å, β = 104.8730(10)°, Z = 4, space group P21/n. The structures were solved by direct methods and refined by full-matrix least-squares procedures to R(F, I [Formula: see text] 3σ(I)) = 0.049, 0.047, 0.042, and 0.047, respectively, for CCD data for 5d, 9a, 11b, and 19. The four molecules contain five-, seven-, six-, and five-membered rings, respectively, with O-B-N groups in the 5d, 11b, and 19, and O-B-O in 9a; the rings exhibit various deviations from planarity, particularly the seven-membered ring.Key words: diarylboron chelates, hydroxyoximes, hydroxynitrones, carboxyoximes, carboxynitrones, organoboron compounds, crystal structure.


2014 ◽  
Vol 10 ◽  
pp. 890-896 ◽  
Author(s):  
Dominik Lenhart ◽  
Thorsten Bach

N-Methyl-N-((trimethylsilyl)methyl)aniline was employed as reagent in visible-light-induced, iridium-catalyzed addition reactions to cyclic α,β-unsaturated carbonyl compounds. Typical reaction conditions included the use of one equivalent of the reaction substrate, 1.5 equivalents of the aniline and 2.5 mol % (in MeOH) or 1.0 mol % (in CH2Cl2) [Ir(ppy)2(dtbbpy)]BF4 as the catalyst. Two major reaction products were obtained in combined yields of 30–67%. One product resulted from aminomethyl radical addition, the other product was a tricyclic compound, which is likely formed by attack of the intermediately formed α-carbonyl radical at the phenyl ring. For five-membered α,β-unsaturated lactone and lactam substrates, the latter products were the only products isolated. For the six-membered lactones and lactams and for cyclopentenone the simple addition products prevailed.


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