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
Synthesis and Crystal Structure of Unexpected...
Williams, Steven Gareth; Bhadbhade, Mohan; Bishop, Roger; Ung, Alison Thavary
2017-07-19 00:00:00
The reaction of ()--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) , and 110.16 (3).
http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.pngAustralian Journal of ChemistryCSIRO Publishinghttp://www.deepdyve.com/lp/csiro-publishing/synthesis-and-crystal-structure-of-unexpected-1s-4r-5r-6s-4-cyano-2-2-y460biEqjR
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
The reaction of ()--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) , and 110.16 (3).
Journal
Australian Journal of Chemistry
– CSIRO Publishing
To get new article updates from a journal on your personalized homepage, please log in first, or sign up for a DeepDyve account if you don’t already have one.
All DeepDyve websites use cookies to improve your online experience. They were placed on your computer when you launched this website. You can change your cookie settings through your browser.