Synthesis and crystal structure of unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl acetate

Williams, SG; Bhadbhade, M; Bishop, R; Ung, AT

Synthesis and crystal structure of unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl acetate

Williams, SG

Bhadbhade, M Bishop, R Ung, AT

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Publication Type:: Journal Article
Citation:: Australian Journal of Chemistry, 2017, 70 (12), pp. 1269 - 1273
Issue Date:: 2017-01-01

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Field	Value	Language
dc.contributor.author	Williams, SG https://orcid.org/0000-0003-4647-436X	en_US
dc.contributor.author	Bhadbhade, M	en_US
dc.contributor.author	Bishop, R	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.date.issued	2017-01-01	en_US
dc.identifier.citation	Australian Journal of Chemistry, 2017, 70 (12), pp. 1269 - 1273	en_US
dc.identifier.issn	0004-9425	en_US
dc.identifier.uri	http://hdl.handle.net/10453/116573
dc.description.abstract	The reaction of (-)-β-pinene with KCN under a mild bridged Ritter reaction gave (1S,5R,6S)-2,2,6-trimethyl-3-aza-bicyclo[3.3.1]non-3-en-6-yl acetate that subsequently reacted to provide an unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonane-6-yl acetate. The structure of the compound was determined by high-resolution mass spectrometry, and IR and NMR spectroscopy and confirmed by single crystal X-ray crystallography. The compound crystallises in the monoclinic P21 space group, with unit cell parameters a 8.6120 (17), b 7.4570 (15), c 11.189 (2) Å, and β 110.16 (3)°.	en_US
dc.relation.ispartof	Australian Journal of Chemistry	en_US
dc.relation.isbasedon	10.1071/CH17270	en_US
dc.subject.classification	General Chemistry	en_US
dc.title	Synthesis and crystal structure of unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl acetate	en_US
dc.type	Journal Article
utslib.citation.volume	12	en_US
utslib.citation.volume	70	en_US
utslib.for	0301 Analytical Chemistry	en_US
utslib.for	03 Chemical Sciences	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	open_access
pubs.issue	12	en_US
pubs.publication-status	Published	en_US
pubs.volume	70	en_US

Abstract:

The reaction of (-)-β-pinene with KCN under a mild bridged Ritter reaction gave (1S,5R,6S)-2,2,6-trimethyl-3-aza-bicyclo[3.3.1]non-3-en-6-yl acetate that subsequently reacted to provide an unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonane-6-yl acetate. The structure of the compound was determined by high-resolution mass spectrometry, and IR and NMR spectroscopy and confirmed by single crystal X-ray crystallography. The compound crystallises in the monoclinic P21 space group, with unit cell parameters a 8.6120 (17), b 7.4570 (15), c 11.189 (2) Å, and β 110.16 (3)°.

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http://hdl.handle.net/10453/116573