A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane.
A diazonium ion derived from 18-aminoandrostane rearranged upon decomposition by a carbonium and a carbenium ion to furnish a mixture of a cyclopropanated compound and two D-homo-androstenes. Hydrogenation of this mixture gave the saturated hydrocarbons, 18-nor-D-homo-androstane and 5a,14ß-androstan...
| Main Authors: | , , , , |
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| Format: | Journal Article |
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Wiley - V C H Verlag GmbH & Co. KGaA
2015
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| Online Access: | http://hdl.handle.net/20.500.11937/39649 |
| _version_ | 1848755648339116032 |
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| author | Bender, M. Schmidtmann, M. Summons, Roger Rullkötter, J. Christoffers, J. |
| author_facet | Bender, M. Schmidtmann, M. Summons, Roger Rullkötter, J. Christoffers, J. |
| author_sort | Bender, M. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | A diazonium ion derived from 18-aminoandrostane rearranged upon decomposition by a carbonium and a carbenium ion to furnish a mixture of a cyclopropanated compound and two D-homo-androstenes. Hydrogenation of this mixture gave the saturated hydrocarbons, 18-nor-D-homo-androstane and 5a,14ß-androstane, which are both fossil sterane biomarkers in Neoproterozoic crude oil. The so far unknown constitution and configuration as well as the geochemical genesis were established by this experiment. The starting material for this investigation, 18-aminoandrostane, was prepared in twelve steps from androstan-17-one (12.5% overall yield) with a Barton reaction as the key step. |
| first_indexed | 2025-11-14T08:59:39Z |
| format | Journal Article |
| id | curtin-20.500.11937-39649 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T08:59:39Z |
| publishDate | 2015 |
| publisher | Wiley - V C H Verlag GmbH & Co. KGaA |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-396492017-09-13T14:29:24Z A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane. Bender, M. Schmidtmann, M. Summons, Roger Rullkötter, J. Christoffers, J. A diazonium ion derived from 18-aminoandrostane rearranged upon decomposition by a carbonium and a carbenium ion to furnish a mixture of a cyclopropanated compound and two D-homo-androstenes. Hydrogenation of this mixture gave the saturated hydrocarbons, 18-nor-D-homo-androstane and 5a,14ß-androstane, which are both fossil sterane biomarkers in Neoproterozoic crude oil. The so far unknown constitution and configuration as well as the geochemical genesis were established by this experiment. The starting material for this investigation, 18-aminoandrostane, was prepared in twelve steps from androstan-17-one (12.5% overall yield) with a Barton reaction as the key step. 2015 Journal Article http://hdl.handle.net/20.500.11937/39649 10.1002/chem.201502148 Wiley - V C H Verlag GmbH & Co. KGaA restricted |
| spellingShingle | Bender, M. Schmidtmann, M. Summons, Roger Rullkötter, J. Christoffers, J. A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane. |
| title | A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane. |
| title_full | A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane. |
| title_fullStr | A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane. |
| title_full_unstemmed | A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane. |
| title_short | A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18-nor-D-homo-Androstane and 5a,14ß-Androstane. |
| title_sort | geomimetic approach to the formation and identification of fossil sterane biomarkers in crude oil: 18-nor-d-homo-androstane and 5a,14ß-androstane. |
| url | http://hdl.handle.net/20.500.11937/39649 |