78631-73-9

Upstream product

• 121525-02-8 2-Chloro-2-(⁽²⁾H₃)-methyl-1-phenyl-(3,3,3-⁽²⁾H₃)-propane 
• 611-70-1 phenyl isopropyl ketone 
• 67-56-1 methanol 

Relevant academic research and scientific papers

Palladium-Catalyzed Synthesis of Deuterated Alkenes through Deuterodechlorination of Alkenyl Chlorides

The palladium-catalyzed deuterodechlorination of alkenyl chlorides has been developed, and a variety of deuterated alkenes were synthesized with precise control of the deuterium incorporation. This catalytic process tolerates heterocyclic moieties and frameworks derived from bioactive agents. In addition to the double incorporation of deuterium, the gram-scale synthesis of a deuterated iminostilbene unit including a core substructure of carbamazepine was achieved in a high yield with an excellent degree of deuteration.

Borderline between E1 and E2 Mechanisms. Bimolecular Base-Promoted Elimination via Ion Pairs Competing with Concerted E2 Elimination

The solvolysis of 2-chloro-2-methyl-1-phenylpropane (1) in methanol or in 25 vol percent acetonitrile in water at 25 deg C yields substitution product 2 (ether or alcohol) and the two elimination products 3 and 4.The olefin fraction in the aqueous solution does not increase significantly in the presence of 0.75 M sodium hydroxide.In methanol, on the other hand, the fraction of 3 and 4, the ratio /, and the rate of disappearance of 1 increase with methoxide ion concentration.The kinetic isotope effects (k12H + k13H + k14H)/(k12d2 + k13d2 +k14d2) = 1.41 and 1.42, measured for the solvolysis of the dideuterated analogue d2-1 in water/acetonitrile and in methanol, respectively, are too large to be secondary effects on a rate-limiting ionization step, but they suggest reaction via a reversibly formed carbocationic intermediate.The solvolysis of the hexadeuterated analogue d6-1 exhibits "normal" secondary kinetic isotope effects, (k12H + k13H + k14H)/(k12d6 + k13d6 + k14d6) = 1.79 and 1.81 in water/acetonitrile and methanol, respectively.The presence of 2 M NaOMe increases the isotope effect for d2-1 to 2.4 but decreases the effect for d6-1 to 1.35.These results indicate that 3 is formed by a parallel methoxide-promoted one-step concerted rout (E2) and that such a route is not significant for the formation of 4.The isotope effect for the E2 reaction is estimated as kH/kd2 = 4.9 (on the basis of the assumption that the elimination product ratio / for the carbocationic route is not affected by MeO(1-)).

PHOSPHORUS CHEMISTRY. III PREPARATION OF VINYL DEUTERATED TRISUBSTITUTED ALKENES

A facile procedure for the preparation of vinyl deuterated trisubstituted alkenes via reduction of the corresponding (2-oxoalkyl)triphenylphosphonium halides with sodium borohydride is described.