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A Geomimetic Approach to the Formation and Identification of Fossil Sterane Biomarkers in Crude Oil: 18‐ nor ‐ D ‐ homo ‐Androstane and 5α,14β‐Androstane
Author(s) -
Bender Matthias,
Schmidtmann Marc,
Summons Roger E.,
Rullkötter Jürgen,
Christoffers Jens
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502148
Subject(s) - androstane , sterane , chemistry , carbonium ion , crude oil , yield (engineering) , chromatography , organic chemistry , stereochemistry , geology , hopanoids , ion , petroleum engineering , paleontology , materials science , structural basin , source rock , metallurgy
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 5α,14β‐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.