Journal article

Publication year: 2014

Pages: 787-798

Journal: Synthesis: Journal of Synthetic Organic Chemistry

Volume number: 46

Issue number: 6

DOI Link: https://doi.org/10.1055/s-0033-1338583

Publisher: Thieme Publishing / Georg Thieme Verlag

Abstract: 

We present an effective three-step chromatography-free sequence for the preparation of apical monohydroxy derivatives of diamantane, triamantane, and [121]tetramantane from the corresponding bis-apical diols utilizing tert-butyldimethylsilyl chloride as the monosilylating agent. The procedure was successfully applied to the monoprotection of several other aliphatic and aromatic diols. Additionally, 9-aminodiamantan-4-carboxylic acid, which has significant potential in medicinal and material sciences, was prepared through Ritter reaction of 4,9-dihydroxydiamantane in trifluoroacetic acid.

Harvard Citation style: Kahl, P., Tkachenko, A., Novikovsky, A., Becker, J., Dahl, J., Carlson, R., et al. (2014) Efficient Preparation of Apically Substituted Diamondoid Derivatives, Synthesis: Journal of Synthetic Organic Chemistry, 46(6), pp. 787-798. https://doi.org/10.1055/s-0033-1338583

APA Citation style: Kahl, P., Tkachenko, A., Novikovsky, A., Becker, J., Dahl, J., Carlson, R., Fokin, A., & Schreiner, P. (2014). Efficient Preparation of Apically Substituted Diamondoid Derivatives. Synthesis: Journal of Synthetic Organic Chemistry. 46(6), 787-798. https://doi.org/10.1055/s-0033-1338583