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Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations
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| Zeitschriftentitel: | European Journal of Organic Chemistry |
|---|---|
| Personen und Körperschaften: | , , , , , , , , |
| In: | European Journal of Organic Chemistry, 2009, 2009, 24, S. 4135-4142 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Hartung, Jens Daniel, Kristina Bergsträßer, Uwe Kempter, Irina Schneiders, Nina Danner, Steffen Schmidt, Philipp Svoboda, Ingrid Fuess, Hartmut Hartung, Jens Daniel, Kristina Bergsträßer, Uwe Kempter, Irina Schneiders, Nina Danner, Steffen Schmidt, Philipp Svoboda, Ingrid Fuess, Hartmut |
|---|---|
| author |
Hartung, Jens Daniel, Kristina Bergsträßer, Uwe Kempter, Irina Schneiders, Nina Danner, Steffen Schmidt, Philipp Svoboda, Ingrid Fuess, Hartmut |
| spellingShingle |
Hartung, Jens Daniel, Kristina Bergsträßer, Uwe Kempter, Irina Schneiders, Nina Danner, Steffen Schmidt, Philipp Svoboda, Ingrid Fuess, Hartmut European Journal of Organic Chemistry Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations Organic Chemistry Physical and Theoretical Chemistry |
| author_sort |
hartung, jens |
| spelling |
Hartung, Jens Daniel, Kristina Bergsträßer, Uwe Kempter, Irina Schneiders, Nina Danner, Steffen Schmidt, Philipp Svoboda, Ingrid Fuess, Hartmut 1434-193X 1099-0690 Wiley Organic Chemistry Physical and Theoretical Chemistry http://dx.doi.org/10.1002/ejoc.200900069 <jats:title>Abstract</jats:title><jats:p>Synthetic, spectroscopic, and structural investigations provided evidence that distinguished neat 3‐alkoxy‐4‐(<jats:italic>p</jats:italic>‐chlorophenyl)‐1,3‐thiazole‐2(3<jats:italic>H</jats:italic>)‐thiones (CPTTORs), once developed to serve as alkoxyl radical precursors for storage and use on demand, showed background reactivity. Selectivity in these transformations was guided by the nature of the <jats:italic>O</jats:italic>‐alkyl substituent. Two pathways reflected the inherent weakness of the N,O bond, leading to products of isomerization and rearrangement. In a third instance, methyl translocation from oxygen to sulfur occurred to furnish a heteroaromatic <jats:italic>N</jats:italic>‐oxide at the expense of a cross conjugated π‐system. Consistent X‐ray crystallographic data sets served as a basis for electronic structure method assessment in order to model aspects relevant to structure and decomposition chemistry that were not available from diffraction data.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p> Lessons of 3‐Alkoxy‐4‐(<i>p</i>‐chlorophenyl)‐1,3‐thiazole‐2(3<i>H</i>)‐thione Chemistry Learned from Structural Investigations European Journal of Organic Chemistry |
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| title |
Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_unstemmed |
Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_full |
Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_fullStr |
Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_full_unstemmed |
Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_short |
Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_sort |
lessons of 3‐alkoxy‐4‐(<i>p</i>‐chlorophenyl)‐1,3‐thiazole‐2(3<i>h</i>)‐thione chemistry learned from structural investigations |
| topic |
Organic Chemistry Physical and Theoretical Chemistry |
| url |
http://dx.doi.org/10.1002/ejoc.200900069 |
| publishDate |
2009 |
| physical |
4135-4142 |
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<jats:title>Abstract</jats:title><jats:p>Synthetic, spectroscopic, and structural investigations provided evidence that distinguished neat 3‐alkoxy‐4‐(<jats:italic>p</jats:italic>‐chlorophenyl)‐1,3‐thiazole‐2(3<jats:italic>H</jats:italic>)‐thiones (CPTTORs), once developed to serve as alkoxyl radical precursors for storage and use on demand, showed background reactivity. Selectivity in these transformations was guided by the nature of the <jats:italic>O</jats:italic>‐alkyl substituent. Two pathways reflected the inherent weakness of the N,O bond, leading to products of isomerization and rearrangement. In a third instance, methyl translocation from oxygen to sulfur occurred to furnish a heteroaromatic <jats:italic>N</jats:italic>‐oxide at the expense of a cross conjugated π‐system. Consistent X‐ray crystallographic data sets served as a basis for electronic structure method assessment in order to model aspects relevant to structure and decomposition chemistry that were not available from diffraction data.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p> |
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| author | Hartung, Jens, Daniel, Kristina, Bergsträßer, Uwe, Kempter, Irina, Schneiders, Nina, Danner, Steffen, Schmidt, Philipp, Svoboda, Ingrid, Fuess, Hartmut |
| author_facet | Hartung, Jens, Daniel, Kristina, Bergsträßer, Uwe, Kempter, Irina, Schneiders, Nina, Danner, Steffen, Schmidt, Philipp, Svoboda, Ingrid, Fuess, Hartmut, Hartung, Jens, Daniel, Kristina, Bergsträßer, Uwe, Kempter, Irina, Schneiders, Nina, Danner, Steffen, Schmidt, Philipp, Svoboda, Ingrid, Fuess, Hartmut |
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| description | <jats:title>Abstract</jats:title><jats:p>Synthetic, spectroscopic, and structural investigations provided evidence that distinguished neat 3‐alkoxy‐4‐(<jats:italic>p</jats:italic>‐chlorophenyl)‐1,3‐thiazole‐2(3<jats:italic>H</jats:italic>)‐thiones (CPTTORs), once developed to serve as alkoxyl radical precursors for storage and use on demand, showed background reactivity. Selectivity in these transformations was guided by the nature of the <jats:italic>O</jats:italic>‐alkyl substituent. Two pathways reflected the inherent weakness of the N,O bond, leading to products of isomerization and rearrangement. In a third instance, methyl translocation from oxygen to sulfur occurred to furnish a heteroaromatic <jats:italic>N</jats:italic>‐oxide at the expense of a cross conjugated π‐system. Consistent X‐ray crystallographic data sets served as a basis for electronic structure method assessment in order to model aspects relevant to structure and decomposition chemistry that were not available from diffraction data.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p> |
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| spelling | Hartung, Jens Daniel, Kristina Bergsträßer, Uwe Kempter, Irina Schneiders, Nina Danner, Steffen Schmidt, Philipp Svoboda, Ingrid Fuess, Hartmut 1434-193X 1099-0690 Wiley Organic Chemistry Physical and Theoretical Chemistry http://dx.doi.org/10.1002/ejoc.200900069 <jats:title>Abstract</jats:title><jats:p>Synthetic, spectroscopic, and structural investigations provided evidence that distinguished neat 3‐alkoxy‐4‐(<jats:italic>p</jats:italic>‐chlorophenyl)‐1,3‐thiazole‐2(3<jats:italic>H</jats:italic>)‐thiones (CPTTORs), once developed to serve as alkoxyl radical precursors for storage and use on demand, showed background reactivity. Selectivity in these transformations was guided by the nature of the <jats:italic>O</jats:italic>‐alkyl substituent. Two pathways reflected the inherent weakness of the N,O bond, leading to products of isomerization and rearrangement. In a third instance, methyl translocation from oxygen to sulfur occurred to furnish a heteroaromatic <jats:italic>N</jats:italic>‐oxide at the expense of a cross conjugated π‐system. Consistent X‐ray crystallographic data sets served as a basis for electronic structure method assessment in order to model aspects relevant to structure and decomposition chemistry that were not available from diffraction data.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p> Lessons of 3‐Alkoxy‐4‐(<i>p</i>‐chlorophenyl)‐1,3‐thiazole‐2(3<i>H</i>)‐thione Chemistry Learned from Structural Investigations European Journal of Organic Chemistry |
| spellingShingle | Hartung, Jens, Daniel, Kristina, Bergsträßer, Uwe, Kempter, Irina, Schneiders, Nina, Danner, Steffen, Schmidt, Philipp, Svoboda, Ingrid, Fuess, Hartmut, European Journal of Organic Chemistry, Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations, Organic Chemistry, Physical and Theoretical Chemistry |
| title | Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_full | Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_fullStr | Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_full_unstemmed | Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_short | Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| title_sort | lessons of 3‐alkoxy‐4‐(<i>p</i>‐chlorophenyl)‐1,3‐thiazole‐2(3<i>h</i>)‐thione chemistry learned from structural investigations |
| title_unstemmed | Lessons of 3‐Alkoxy‐4‐(p‐chlorophenyl)‐1,3‐thiazole‐2(3H)‐thione Chemistry Learned from Structural Investigations |
| topic | Organic Chemistry, Physical and Theoretical Chemistry |
| url | http://dx.doi.org/10.1002/ejoc.200900069 |