TY - JOUR
T1 - Synthesis of Biological Markers in Fossil Fuels. 1. 17a and Isomers of 30-Norhopane and 30-Normoretane
AU - Bauer, Philip E.
AU - Dunlap, Norma K.
AU - Arseniyadis, Siméon
AU - Watt, David S.
AU - Seifert, Wolfgang K.
AU - Moldowan, J. Michael
PY - 1983/12
Y1 - 1983/12
N2 - 21-Hydroxyhopan-3-one was converted to a mixture of 22,29,30-trinor-17a-hopan-21-one and 30-norhopan-22-one by the following reaction sequence: (1) dehydration with phosphorus oxytrichloride, (2) Wolff-Kishner reduction, and (3) ozonolysis. These two ketones were then utilized to prepare various pentacyclic C29H50 hydrocarbons used as biological markers in correlating crude oils and souree rocks. 30-Norhopan-22-one was converted to 30-norhopane and 30-normoretane. 22,29,30-Trinor-17a-hopan-21-one was converted to 30-nor-17a-hopane and 30-nor-17α-moretane. The key synthetic feature of these transformations was the efficient application of Barton's tri-n-butyltin hydride reduction of S-methyl xanthates in order to secure the desired hydrocarbons. The identitiy of synthetic 30-norhopane, 30-normoretane, and 30-nor-17α-hopane with their naturally occurring counterparts was demonstrated by gas chromatography-mass spectrometry. The thermodynamically least stable isomer, 30-nor-17a-moretane, if present at all, was limited to small quantities in fossil fuels.
AB - 21-Hydroxyhopan-3-one was converted to a mixture of 22,29,30-trinor-17a-hopan-21-one and 30-norhopan-22-one by the following reaction sequence: (1) dehydration with phosphorus oxytrichloride, (2) Wolff-Kishner reduction, and (3) ozonolysis. These two ketones were then utilized to prepare various pentacyclic C29H50 hydrocarbons used as biological markers in correlating crude oils and souree rocks. 30-Norhopan-22-one was converted to 30-norhopane and 30-normoretane. 22,29,30-Trinor-17a-hopan-21-one was converted to 30-nor-17a-hopane and 30-nor-17α-moretane. The key synthetic feature of these transformations was the efficient application of Barton's tri-n-butyltin hydride reduction of S-methyl xanthates in order to secure the desired hydrocarbons. The identitiy of synthetic 30-norhopane, 30-normoretane, and 30-nor-17α-hopane with their naturally occurring counterparts was demonstrated by gas chromatography-mass spectrometry. The thermodynamically least stable isomer, 30-nor-17a-moretane, if present at all, was limited to small quantities in fossil fuels.
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U2 - 10.1021/jo00172a010
DO - 10.1021/jo00172a010
M3 - Article
AN - SCOPUS:0001565726
SN - 0022-3263
VL - 48
SP - 4493
EP - 4497
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -