Synthesis of bicyclic compounds by cationic [pi]-cyclization /
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| Other Authors: | |
| Format: | Thesis Book |
| Language: | English |
| Published: |
[College Station, Tex.] :
Cooper,
1978.
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| Subjects: | |
| Online Access: | Link to ProQuest copy. Link to OAKTrust copy |
| Abstract: | The basic goal of this study was the development and utilization of new methodology for synthesis of bicycle[5.4.0]undecanes, bicycle[4.4.0]decanes, bicycle[4.3.0]nonanes, and spiro[5.5]undecanes. The three aspects investigates were: a) enone functionality as an initiator for cationic po-cyclization, b) pi-participants for selective formation of 5-, 5-, and 7-membered rings, and c) stereoselective formation of spirocyclic compounds. The synthesis of bibyblic keto alcohols 5,1 57, and 63 represents the successful utilization of enones as initiators for cationic pi-cyclizations. Conversion of keto alcohol 51 into the known keto 53 is a demonstration of the synthetic utility of this cyclization methodology. Various pi-participants were studied in order to gain a better understanding of the requirements for the selective formation of 5-, 6-, and 7-membered rings. Cyclization of enones 6 and 7 gave 5- and 6-membered ring products as predicted from results of prior cyclization studies. Cylclization of [gamma]-allenyl enones 5a and 5b gave products which were significantly different. Enone 5a gave only products containing a decalin ring skeleton whereas enone 5b gave only products containing a hydrindane ring skeleton. A rationalization for these divergent results is presented. |
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| Item Description: | "Major subject: Chemistry." Vita. |
| Physical Description: | xii, 145 leaves : illustrations ; 28 cm |
| Bibliography: | Includes bibliographical references (leaves 136-144). |