628-16-0Relevant articles and documents
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Farmer,Lossing
, p. 861,866 (1955)
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The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis
Garbacz, Mateusz,Stecko, Sebastian
supporting information, p. 3213 - 3222 (2020/07/06)
A mild, and versatile, organophotoredox/Ni-mediated protocol was developed for the direct preparation of diverse, enantioenriched allyl carbamates. The reported approach represents a significant departure from classical step-by-step synthesis of allyl carbamates. This dual photoredox/Ni based strategy offers unrivalled capacity for convergent unification of readily available alkyl halides and chiral carbamates derived from 1-bromo-alken-3-ols with high chemoselectivity and efficiency. The reported photoredox/Ni catalyzed cross-coupling reaction is not limited to carbamates, but also to other O-derivatives such as esters, ethers, acetals, carbonates or silyl ethers. To demonstrate the utility of the reported protocol, the resulting allyl carbamates were transformed into functionalized non-racemic allylamines through a sigmatropic rearrangement reaction in enantiospecific manner. This approach allowed for synthesis of enantiomeric allylamines by a simple control of the geometry of a double bond of allyl carbamates. (Figure presented.).
Pressure and Temperature Effects on Product Channels of the Propargyl (HC≡CCH2) Combination Reaction and the Formation of the First Ring
Howe, Pui-Teng,Fahr, Askar
, p. 9603 - 9610 (2007/10/03)
The mechanism for formation of aromatic and polyaromatic hydrocarbons and soot in combustion processes is still far from being well understood. The formation of the first aromatic ring, particularly benzene, is thought to be a critical step in soot formation mechanisms and has been the subject of continuing interest. Experimental results on the nature and the relative yields of the final products of the propargyl combination, C3H3 + C3H3 → C6H6 (1) were presented. Propargyl radicals, for most experiments, were generated by the 248 nm excimer laser photolysis of propargyl bromide. Five isomeric C6H6 final products were detected including 1,5-hexadiyne, fulvene, dimethylenecyclobutene, and benzene. The formation of dimethylenecyclobutene and benzene from the propargyl combination reaction was significantly more efficient than previously predicted. The relative yield of fulvene was less than those of dimethylenecyclobutene and benzene.
Enantioselective total synthesis of (+)-testudinariol A using a new nickel-catalyzed allenyl aldehyde cyclization
Amarasinghe, Kande K. D.,Montgomery, John
, p. 9366 - 9367 (2007/10/03)
An enantioselective total synthesis of (+)-testudinariol A was completed. A new nickel-catalyzed allenyl aldehyde cyclization was developed in the approach. In addition, an asymmetric anti aldol reaction and a two-directional oxocarbenium ion/vinyl silane condensation were employed as key steps. Copyright
