Preparation,Reactions, and NMR Studies of 4-Methyl-4-Phospha-Tetracyclo [3.3.0.02,8.03,8] Octane 4-Oxide and Derivatives |
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| Authors: | S E Cremer J M Cowles F R Farr P W Kremer H Hwang A C Peterson |
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| Institution: | Marquette University, Dept. of Chemistry , Milwaukee , WI , 53233 |
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| Abstract: | Abstract The title compound which we1 and others2 have previously synthesized has now been extensively investigated. The tetracyclic phosphonium chloride 1 was prepared by treatment of norbornadiene with CH3PCl2 at 65–80°C for one week. Treatment of 1 with AICl3/CH2CI2 gave 2. Direct or “Inverse” addition at water to 2 dictated the stereochemistry of the oxide 3. Stereoassignments of 3 were made based on lanthanide shift ?1H and 13C nmr studies studies. Extensive 2-D nmr studies (HETCOR, COSY) and triple irradiation experiments enabled chemical shift and coupling constant assignments. |
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