SYNTHESIS OF AND CONFORMATIONAL STUDIES ON N-ALKYL-3-THIA-7-AZABICYCLO [3.3.1]NONAN-9-ONES AND DERIVATIVES. A SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS OF 2,2,4,4-TETRAMETHYL-6,8-DIPHENYL-3-THIA-7-AZABICYCLO [3.3.1]-NONAN-9-ONE |
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| Authors: | Bruce R Bailey III K Darrell Berlin Douglas R Powell Dick Van der Helm |
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| Institution: | 1. Department of Chemistry , Oklahoma State University , Stillwater, OK, 74078;2. Department of Chemistry , University of Oklahoma , Norman, OK, 73109 |
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| Abstract: | Abstract A series of N-alkyl-3-thia-7-azabicyclo3.3.1]nonan-9-ones and derivatives have been prepared from the reaction of an appropriate 4-thianone, an aldehyde and an amine in a Mannich type condensation. Reduction of the ketones via Wolff-Kishner conditions produced bicyclic systems with the methylene bridging group. Addition of Grignard reagents to the ketones did yield the expected alcohols. Conformational analysis of the systems was performed via diagnosis of the 1H and 13C NMR spectra. A single crystal X-ray diffraction analysis of 2,2,4,4-tetramethyl-6,8-diphenyl-3-thia-7-azabicyclo3.3.1]nonan-9-one was accomplished and revealed a boat conformer for the nitrogen-containing ring and a chair conformer for the sulfur-containing ring. The ketone crystallized in the triclinic space group P1 (Z=2) with a=6.216 (3), b=10.507 (5), c=15.335 (6) Å, α=86.64 (4), β=86.66 (4), and γ=98.51 (5)° Vol=986.55 Å3]. |
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