693-02-7Relevant articles and documents
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Smith et al.
, p. 3560,3562 (1960)
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Relative Migratory Aptitudes of Alkyl Groups in the Iodination of Lithium Ethynyltrialkylborates
Slayden, Suzanne W.
, p. 2311 - 2314 (1981)
Relative migratory aptitudes of various alkyl groups have been determined in the iodine-induced rearrangement of lithium ethynyltrialkylborates.Trialkylboranes of types R3-nBR'n and thexyl-BRR' were complexed with lithium acetylide-ethylenediamine.Iodination, followed by deiodoboration of the rearranged intermediates, produced 1-alkynes in amounts which depend, after statistical correction, on the relative rates of alkyl group migration in an intramolecular competition.In some cases, the migratory aptitude was found to depend on the alkyl substitution pattern in the organoborate.The overall migratory aptitude order is bicyclooctyl > n-butyl > cyclohexyl, isobutyl, sec-butyl > thexyl.When the secondary and primary migrating carbon series are considered separately, the order is consistently bicyclooctyl > cyclohexyl > sec-butyl, and n-butyl > isobutyl.
Method for synthesizing terminal alkyne by utilizing 1, 2-dihaloalkane
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Paragraph 0022-0024, (2020/04/29)
The invention discloses a method for synthesizing terminal alkyne by utilizing 1, 2-dihaloalkane. According to the method, 1, 3-dihaloalkane is used as a raw material and terminal alkyne is synthesized under the action of alkali and a catalyst, wherein the molar ratio of the alkali to the 1, 2-dihaloalkane is 2: 1-5: 1, the use amount of the catalyst is 2%-10% of the mass of the 1, 2-dihaloalkane,the reaction temperature is 100-150 DEG C and the reaction time is 3-10 h. The method has the advantages of environmental protection, high selectivity, high yield and the like.
Na2S-mediated synthesis of terminal alkynes from: Gem -dibromoalkenes
Singh, Radhey M.,Nandini, Durgesh,Bharadwaj, Kishor Chandra,Gupta, Tanu,Singh, Raj Pal
, p. 9979 - 9982 (2017/12/26)
The Na2S-mediated facile synthesis of terminal alkynes from gem-dibromoalkenes, at 20/40 °C under open flask conditions has been developed. Various precursors derived from heteroaromatic/aromatic/aliphatic aldehydes were found compatible. The reaction is proposed to proceed through the Fritsch-Buttenberg-Wiechell (FBW) rearrangement involving the corresponding vinyl carbene. Using mild reaction conditions with inexpensive Na2S·9H2O under air atmosphere has significant advantages over earlier routes.