19543-61-4

Basic information

• Product Name: (1S,3S,4S,5R,7R)-4-Chloroadamantan-2-one
• Synonyms: (1S,3S,4S,5R,7R)-4-Chloroadamantan-2-one
• CAS NO: 19543-61-4
• Molecular Weight: 0
• Mol File: 19543-61-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,3S,4S,5R,7R)-4-Chloroadamantan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S,4S,5R,7R)-4-Chloroadamantan-2-one(19543-61-4)
• EPA Substance Registry System: (1S,3S,4S,5R,7R)-4-Chloroadamantan-2-one(19543-61-4)

Safety Data

• Hazardous Substances Data: 19543-61-4(Hazardous Substances Data)

Upstream product

• 21898-84-0 4-oxohomoadamantan-5-one 
• 5202-69-7 (+)-(1R)-2-carboxyadamantane-4,8-dione 
• 19439-22-6 (1S)-4(a)-Brom-adamantanon-⁽²⁾ 
• 19624-15-8 (1S)-4(e)-Brom-adamantanon-⁽²⁾ 
• 700-58-3 2-Adamantanone 
• 21932-98-9 endo-Bicyclo<3.3.1>non-6-ene-3-carboxylic acid 
• 26278-43-3 4^a-Hydroxytricyclo<3.3.1.1^3,7>decan-2-on 
• 594-19-4 tert.-butyl lithium 
• 19213-96-8 4^e-chloro-2-adamantanone 
• 19213-96-8 4e-Chlor-adamantanon-(2) 

Downstream Products

• 19213-96-8 4e-Chlor-adamantanon-(2) 
• 113335-68-5 2,2,4^e-trichloroadamantane 
• 19213-96-8 4^e-chloro-2-adamantanone 
• 113335-68-5 2,2,4^a-trichloroadamantane 
• 95935-36-7 7-endo-pivaloylbicyclo(3.3.1)non-2-ene 
• 132259-84-8 7-endo-(di-tert-butylhydroxymethyl)bicyclo-(3.3.1)non-2-ene 
• 132156-54-8 2,11,11-trimethyl-15-oxa-2,4-ethanoadamantane 
• 132259-88-2 4-endo-tert-butyl-3,4-exo-epoxyprotoadamantane 
• 132156-40-2 2^e-tert-butyl-4^a-chloroadamantan-2^a-ol 

Relevant articles and documents

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

Syntheses and NMR Spectra of Substituted 2-tert-Butyladamantan-2-ols

The synthesis of a number of substituted 2-tert-butyladamantan-2-ols from the corresponding ketones is described.In addition to these addition reactions, some unexpected rearrangements were observed.Reaction mechanisms are proposed to rationalize the experimental results. 13C NMR spectra of some adamantanes are discussed in terms of substituent interaction effects.

REACTION OF 5-OXO-4-OXAHOMOADAMANTANE WITH THIONYL CHLORIDE

On reaction with thionyl chloride 5-oxo-4-oxa-homoadamantane gives rise to a mixture of 4a-chloro- and 4e-chloro-2-adamantanone.The carbonyl group of chloroadamantane further reacts with thionyl chloride under formation of 2,2,4e-trichloroadamantane.In the same way adamantanone reacts with thionyl chloride, giving rise to 2,2-dichloroadamantane.