78679-70-6Relevant articles and documents
Preparation of 1-adamantyl ketones: Structure, mechanism of formation and biological activity of potential by-products
Vicha, Robert,Necas, Marek,Potacek, Milan
, p. 709 - 722 (2008/02/01)
Reactions between adamantane-1-carbonyl chloride and several Grignard reagents as well as interactions with solvents have been examined. Some new and unexpected adamantane derivatives were isolated, fully characterized and their biological activity determined. In particular, an unexpected isochromanone 16 was formed in an SEAr process, in which a stable hydrocarbon was the leaving group.
REACTION OF 1-ADAMANTYL CATION WITH CARBON MONOXIDE IN THE PRESENCE OF ADAMANTANE AND TRIFLUOROMETHANESULFONIC ACID: A CONVENIENT ROUTE TO 3,4-HOMOADAMANTANEDIOL
Takeuchi, Ken'Ichi,Akiyama, Fumio,Miyazaki, Tadakazu,Kitagawa, Itsuko,Okamoto,Kunio
, p. 701 - 710 (2007/10/02)
The carbonylation of the 1-adamantyl cation with carbon monoxide in carbon tetrachloride at atmospheric pressure in the presence of trifluoromethanesulfonic acid (triflic acid) and adamantane affords 3-hydroxy-4-homoadamantyl 1-adamantanecarboxylate (2) in 70percent yield under appropriate conditions.Among various 1-adamantyl cation precursors tested, 1-adamantyl trifluoromethanesulfonate (triflate) and methanesulfonate (mesylate) have given the best, comparable results.As to the acid catalyst, fluorosulfonic acid is less effective than triflic acid, and 100percent sulfuric acid a nd methanesulfonic acid are completely ineffective to produce 2.It is recommended to use five mol each of triflic acid and adamantane per mol of 1-adamantyl mesylate or triflate.This reaction proceeds via the addition of the 1-adamantanecarbynol cation to 1-adamantanecarbaldehyde, a transient intermediate, followed by the Wagner-Meerwein rearrangement.The hydroxy ester 2 is easily converted into 3,4-homoadamantanediol which is a promising starting material for 3,4-bifunctional homoadamantane derivates.
Synthesis of 1-adamantyl and 1-adamantylmethyl alkyl ketones
Grava, I. Ya.,Polis, Ya. Yu.,Lidak, M. Yu.,Liepin'sh, E. E.,Shatts, V. D.,et al.
, p. 679 - 686 (2007/10/02)
The reaction of 1-adamantanecarboxylic and 1-adamantylacetic acids with Grignard reagents in the presence of cuprous chloride or iodide gave the corresponding ketones.