51020-64-5

Upstream product

• 21932-98-9 endo-Bicyclo<3.3.1>non-6-ene-3-carboxylic acid 
• 21898-84-0 4-oxohomoadamantan-5-one 
• 134329-63-8 4(a)-(trifluoromethylsulfonyloxy)adamantan-2-one 

Downstream Products

• 19213-99-1 2,4-Dihydroxyadamantane 
• 134150-35-9 2,4-Dihydroxy-2-isopropyladamantane 
• 19213-98-0 4^e-bromoadamantan-2-one 
• 19213-98-0 4^a-bromoadamantan-2-one 
• 134150-28-0 4-Isopropylidene-2-adamantanone tosylhydrazone lithium salt 
• 19213-99-1 adamantane-2a, 4a-diol 
• 132156-41-3 2^e-tert-butyladamantan-2^a,4^a-diol 
• 132156-55-9 4-tert-butyl-2,11,11-trimethyl-15-oxa-2,4-ethanoadamantane 
• 19213-96-8 4^e-chloroadamantan-2-one 
• 19213-96-8 4^a-chloroadamantan-2-one 
• 113335-68-5 2,2,4^e-trichloroadamantane 
• 19213-99-1 adamantan-2e, 4a-diol 
• 19213-99-1 adamantane-2e, 4e-diol 

Relevant academic research and scientific papers

The nature of the electronic factor governing diastereofacial selectivity in remotely substituted (X) 2-adamantyl cations: 5-X versus 4-X substitution

A limited series of 4eq-substituted (X) 2-methyleneadamantanes (6, Y=CH2, X=F, Cl, Br, I, and SnMe3) has been synthesized and diastereoselectivities for their hydrochlorination (HCl/CH2Cl 2) have been determined. Diastereoselectivities for the fluorination (DAST/CH2Cl2) of secondary alcohol mixtures, obtained from the hydride reduction of the precursor ketones (6,Y=O) to the alkenes, have also been measured. A comparison of this selectivity data for nucleophilic trapping of 4eq-substituted (X) 2-adamantyl cations (4, R=H and Me) with the corresponding information for 5-substituted (X) 2-adamantyl cations (1, R=H and Me) has revealed important distinctions between the two series. In particular, whereas extended hyperconjugative effects appear to be the predominant electronic effect governing facial selectivity in the 5,2-series, electrostatic influences prevail in the 4,2-disposition. Copyright

A Convenient Method for the Preparation of 4(e)-Hydroxy- and 4(e)-Methoxyadamantan-2-ones

Hydrolysis or methanolysis of 4(a)-(trifluoromethylsulfonyloxy)adamantan-2-one affords 4(e)-hydroxy- or 4(e)-methoxyaddamantan-2-one, respectively, as major product, both of which are easily separated from minor by-products.

Synthesis and Hydrolysis of 4-Substituted 2-Adamantyl p-Nitrobenzenesulfonates

Several 4e-substituted 2e- and 2a-adamantyl p-nitrobenzenesulfonates have been prepared by new routes.Their hydrolysis products are described.