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Synthesis of a Particular Ylide from Triethyl Phosphite along with Theoretical and Experimental Studies around its Carbon-Carbon Double Bond: Dynamic ^1H NMR
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نویسنده
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HabibiKhorassani S. M. ,Ansari Fard M. ,Mohammadi M. ,Aghdaei E. ,Shahraki M. ,Hadizadeh M. ,Hazeri N.
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منبع
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jordan journal of chemistry - 2012 - دوره : 7 - شماره : 1 - صفحه:23 -31
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چکیده
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Stable phosphorus ylide was obtained from a simple and efficient one-pot threecomponentreaction between triethyl phosphite and dimethyl acetylenedicarboxylate (dmad) inthe presence of 4,5-dihydrothiazole-2-thiol in a dry diethyl ether at ambient temperature in highyield. the ^1h nmr spectrum of this compound exhibited dynamic effect that is attributed torestricted rotation around the carbon-carbon double bond. the experimental rotational energybarrier (δg^≠) on the basis of ^1h nmr study for the rotational interchangeable process of the two z- and e-isomeres in ylide 4 equal to (63 ± 2) kj.mol^-1. in addition, theoretical study was investigated on the basis of rotation around the carbon-carbon double bond using ab initiomethod at hf/6-31g level of theory. the theoretical rotational energy barrier (82 ± 2) kj.mol^-1 for this interconversion was in agreement with the experimental data.
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کلیدواژه
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Dynamic ^1H NMR; Restricted rotation; HF/6-31G level theory; Triethyl phosphate.
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آدرس
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university of sistan and baluchestan, Department of Chemistry, ایران, university of sistan and baluchestan, Department of Chemistry, ایران, university of sistan and baluchestan, Department of Chemistry, ایران, university of sistan and baluchestan, Department of Chemistry, ایران, university of sistan and baluchestan, Department of Chemistry, ایران, university of sistan and baluchestan, Department of Chemistry, ایران, university of sistan and baluchestan, Department of Chemistry, ایران
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Authors
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