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Thesis
Synthesis of Ethyl 1-Nitro-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenecarboxylate Via a Diels-Alder Pathway
Master of Science (M.S.), Drexel University
May 2014
DOI:
https://doi.org/10.17918/etd-4501
Abstract
Previously, ethyl 1-nitro-1,2,3,5,6,7,8,8a-octahydro-1- naphthalenecarboxylate was synthesized via tandem Mitsunobu cyclization - [3,3]-sigmatropic rearrangement of ethyl 5-(cyclohex-1-en-1-yl)-5-hydroxy-2- nitropentenoate. It was obtained in 48% yield as a 90:10 mixture of diastereomers by this route.1 In this study, ethyl 1-nitro-1,2,3,5,6,7,8,8aoctahydro- 1-naphthalenecarboxylate was obtained by an alternate reaction pathway. The Diels-Alder reaction of ethyl 2-nitro-2-propenoate generated in situ and 1-vinylcyclohexene afforded ethyl 1-nitro-1,2,3,5,6,7,8,8a-octahydro-1- naphthalenecarboxylate in 63% yield as a 70:30 mixture of diastereomers. The same major diastereomer predominated in both the Diels-Alder and tandem cyclization - rearrangement routes. The yield was higher but the stereoselectivity was lower for the Diels- Alder route. Attempts to separate the product diastereomers by chromatography were unsuccessful.
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Details
- Title
- Synthesis of Ethyl 1-Nitro-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenecarboxylate Via a Diels-Alder Pathway
- Creators
- Panagiota Tsetsakos - DU
- Contributors
- Peter A. Wade (Advisor) - Drexel University (1970-)
- Awarding Institution
- Drexel University
- Degree Awarded
- Master of Science (M.S.)
- Publisher
- Drexel University; Philadelphia, Pennsylvania
- Resource Type
- Thesis
- Language
- English
- Academic Unit
- College of Arts and Sciences; Chemistry; Drexel University
- Other Identifier
- 4501; 991014632303404721