Adelaide Research & Scholarship
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https://hdl.handle.net/2440/4901
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| Type: | Journal article |
| Title: | Cage formation in the reaction 7-tert-butoxynorbornadiene with 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole: X-ray structure, AM1 calculations and mechanistic comments |
| Author: | Tiekink, E. Warrener, R. Elsey, G. Russell, R. |
| Citation: | Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry, 1995; 36(29):5275-5278 |
| Publisher: | Pergamon Press |
| Issue Date: | 1995 |
| ISSN: | 0040-4039 |
| Abstract: | MO calculations (AM1) correctly predict the endo-specificity in the reaction of 7-tert-butoxynorbornadiene7 with 2,5-tris(trifluoromethyl) 1,3,5,4-oxadiazole2 which leads onto a cage product 10 (X-Ray structure reported). This result and others is used to develop a working hypothesis for oxadiazole coupling involving Diels-Alder 1:1-adducts, stereoselective dinitrogen elimination and fused 5-oxabicyclo[2.1.0]pentane intermediates. © 1995. |
| DOI: | 10.1016/00404-0399(50)0956D- |
| Published version: | http://dx.doi.org/10.1016/00404-0399(50)0956d- |
| Appears in Collections: | Aurora harvest 6 Chemistry publications |
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