14449-41-3Relevant academic research and scientific papers
SYNTHESIS AND SOME REACTIONS OF 1-ADAMANTYL TRIFLUOROMETHANESULFONATE
Takeuchi, Ken'ichi,Moriyama, Takamasa,Kinoshita, Tomomi,Tachino, Hitoshi,Okamoto, Kunio
, p. 1395 - 1398 (1980)
1-Adamantyl trifluoromethanesulfonate (1) has been prepared from 1-bromoadamantane and silver trifluoromethanesulfonate in 2,2-dimethylbutane.The trifluoromethanesulfonate (1) abstracts hydride from pentane or hexane to form adamantane, initiates ring-opening polymerization of tetrahydrofuran, and reacts with alkyllithiums to afford 1-alkyladamantanes.
Cross-Coupling Reaction of tert-Alkyl halides with Grignard Reagents in Dichloromethane as a Non-Lewis Basic Medium
Ohno, Masatomi,Shimizu, Kazuo,Ishizaki, Kenichi,Sasaki, Tadashi,Eguchi, Shoji
, p. 729 - 733 (2007/10/02)
In dichloromethane as a non-Lewis basic solvent, 1-haloadamantane 1 underwent a cross-coupling reaction with Grignard reagents to give bridgehead-substituted products 3-16 in moderate yields.In this case the same kind of halogen in both 1 and a Grignard reagent was favored; if not, functional exchange (i.e., 1a to 1c) occurred first.The reaction using 5-hexenylmagnesium bromide as a radical probe afforded uncyclized/cyclized coupling products in a 6/4 ratio.These fact suggested the significant participation of the single-electron-transfer process in these reactions.The present method could be extended to tert-butylation with some Grignard reagents.Interestingly, 1,3-dichloro-3-methylbutane coupled with butylmagnesium chloride selectively at the tertiary position. for the above displacement reaction of 1, an organozinc was also found to be effective.
Contribution a l'etude des reactions d'alkylation et de polyalkylation de l'adamantane et de ses homologues
Molle, G.,Dubois, J. E.,Bauer, P.
, p. 2428 - 2433 (2007/10/02)
A method for preparing alkyl derivatives of cage-structure compounds is proposed.It relies on the use of Grignard reactions with a high boiling point solvent.The reactions take place at atmospheric pressure.Methylation of adamantane, diamantane, and homoadamantane occurs with quantitative yield.With other primary alkyl groups, yields are better than 60percent.Competition between alkylation and secondary reactions is discussed on the basis of a free radical mechanism.
