109463-66-3Relevant academic research and scientific papers
Facile Synthesis of Cyanide and Isocyanides from CO
Grimme, Stefan,Kooij, Bastiaan,Lin, Jack H.,Qu, Zheng-Wang,Stephan, Douglas W.,Wang, Tongtong,Xu, Maotong
supporting information, p. 16965 - 16969 (2021/06/28)
The reaction of K[N(SiMe3)2] with 13CO proceeds in C6D6 or THF affording K13CN and O(SiMe3)2 under mild conditions as confirmed by crystallographic characterization of K(18-crown-6)CN. Similarly reaction of the alkali metal amides, M[N(SiR3)R′] (M=Li, K; R=Ph, Me; R′=alkyl, aryl) provides the corresponding 13C labeled isocyanide RN13C and MOSiR3, generally in high yields. In some instances, the use of the sterically bulky Ph3Si-substituent is required to preclude 1,2-silyl migration affording the silylcarbamoyl salt M[Me3SiC(O)NR′]. These reactions have been used to obtain 19 examples of 13C labelled isocyanides, and several examples of gram scale reactions are reported. The mechanism of the reactions is probed via reliable DFT calculations.
ORGANOMETALLIC REAGENTS IN SYNTHESIS A NEW PROTOCOL FOR CONSTRUCTION OF THE INDOLE NUCLEUS
Smith, III, Amos B.,Visnick, Melean,Haseltine, John N.,Sprengeler, Paul A.
, p. 2957 - 2970 (2007/10/02)
Organodilithium reagents derived from 2-alkyl-N-trimethylsilyl anilines undergo condensation with esters of carboxylic acids to afford substituted indoles.A total of 16 examples are reported; yields in general were good.In conjuction with this program, a convenient, large-scale procedure for preparation of monosilylated anilines was also developed.To demonstrate the utility of the new indole protocol in natural products synthesis, efficient syntheses of (+)-cinchonamine and (+)-epi-cinchonamine as well as a tetracyclic model system for the architecturally complex penitrem mycotoxins were completed in regio- and stereoselective fashion.
