92863-04-2Relevant academic research and scientific papers
A Domino Strategy for the Synthesis of 2H-Pyrans from Propargyl Vinyl Ethers
Tejedor, David,Delgado-Hernández, Samuel,Diana-Rivero, Raquel,Díaz-Díaz, Abián,García-Tellado, Fernando
, p. 1784 - 1790 (2019/02/19)
Stable monocyclic 2H-pyrans are synthesized from readily available tertiary propargyl vinyl ethers via a metal-free all-pericyclic domino manifold involving a sequential propargyl Claisen rearrangement/[1,3]H-shift/oxa-6π electrocyclization set of reactions. The wide scope of this protocol is exemplified by the synthesis of 21 different 2H-pyrans incorporating a varied substitution pattern at the ring.
Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions
Liu, Yanan,Xie, Peizhong,Sun, Zuolian,Wo, Xiangyang,Gao, Cuiqing,Fu, Weishan,Loh, Teck-Peng
supporting information, p. 5353 - 5356 (2018/09/13)
An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
PROPARGYL ORGANOMETALLIC COMPOUNDS. II. ALKYLATION OF SODIUM DERIVATIVES OF 1-ALKYL-1-ARYL-2-ALKYNES IN LIQUID AMMONIA
Libman, N. N.,Sevryukov, Yu. P.
, p. 68 - 75 (2007/10/02)
In most cases the alkylation of the sodium derivatives of 1-phenyl-1-alkyl-2-alkynes by methyl, ethyl, isopropyl, and tert-butyl bromides in liquid ammonia takes place preferentially at the sp2-hybridized carbon atom, and this leads to the formation of the corresponding acetylenes.The regioselectivity of the reaction is explained by the greater softness of the trigonal atom of the ambident propargyl anion and its smaller screening by the solvate shell compared with the diagonal atom.
