93624-65-8Relevant academic research and scientific papers
Synthesis and ring-opening reaction of novel 1,3-dehydroadamantanes possessing phenyl and alkoxyl substituents
Inomata, Sotaro,Harada, Yusuke,Matsuoka, Shin-Ichi,Ishizone, Takashi
, p. 3238 - 3248 (2013/04/24)
A series of novel 1,3-dehydroadamantanes (DHAs) possessing phenyl or alkoxyl substituents, such as 5-phenyl-1,3-dehydroadamantane, 5-butyl-7-phenyl-1,3-dehydroadamantane, 5-methoxy-1,3-dehydroadamantane, 5-butoxy-1,3-dehydroadamantane, 5-butyl-7-methoxy-1,3-dehydroadamantane, and 5-butoxy-7-butyl-1,3-dehydroadamantane were synthesized and subjected to react with acidic compounds. 1,3-Dibromoadamantanes carrying phenyl or alkoxyl substituents were converted into the corresponding DHAs via the intramolecular Wurtz-type coupling reactions with lithium metal in THF in 23-62% yields. Ring-opening reactions of DHAs readily occurred with acetic acid or methanol under acidic conditions to form various 1-acetoxyadamantanes or 1-methoxyadamantanes containing phenyl or alkoxyl groups. The resulting 1-butyl-3-methoxy-5-phenyladamantane, 1-acetoxy-3-butyl-5-phenyladamantane, 1-acetoxy-3-butyl-5-methoxyadamantane, 1-acetoxy-3-butoxy-5-butyladamantane, and 1-butoxy-3-butyl-5-methoxyadamantane possessed stereogenic center. The high reactivity of the inverted 1,3-carbon-carbon σ-bond in DHAs toward the acidic compounds indicated the high electron density, which was supported by the sp2 character of cyclopropane rings in DHAs estimated by J C-H coupling constants in the 13C NMR analyzes.
Synthese en serie adamantane : preparation d'adamantanes trisubstitues-1,2,3 et -1,2,5 et de protoadamantanones -4 substituees en position -6 ou -8
Drivas, Ioannis,Mison, Pierre
, p. 252 - 264 (2007/10/02)
A regio and diastereospecific synthetic approach to 1,3-dialkyl (and 1,3-diphenyl) adamantanes bearing a functional group in position-2 (7) and to 1,5-dialkyl (and 1,5-diphenyl) 2-adamantanols (syn 8) is described.This has been accomplished through an addition-isomerisation process on two new classes of 4-protoadamantanones bearing a substituent in position 8 or 6 (3 and 4).These have been prepared via an intramolecular base catalysed cyclisation of iodoketones (11), obtained by thermolysis of hypo-iodites (10).
