Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5 + 3] Dimerization versus [5 + 2] Cycloaddition Reactions
Oxidopyrylium ylides are useful intermediates in synthetic organic chemistry because of their capability of forming structurally complex cycloadducts. They can also self-dimerize via [5 + 3] cycloaddition, which is an oft-reported side reaction that can negatively impact [5 + 2] cycloadduct yields a...
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Published in | Journal of organic chemistry Vol. 84; no. 22; pp. 14670 - 14678 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
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American Chemical Society
15.11.2019
Amer Chemical Soc |
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Abstract | Oxidopyrylium ylides are useful intermediates in synthetic organic chemistry because of their capability of forming structurally complex cycloadducts. They can also self-dimerize via [5 + 3] cycloaddition, which is an oft-reported side reaction that can negatively impact [5 + 2] cycloadduct yields and efficiency. In select instances, these dimers can be synthesized and used as the source of oxidopyrylium ylide, although the generality of this process remains unclear. Thus, how the substitution pattern governs both dimerization and cycloaddition reactions is of fundamental interest to probe factors to regulate them. The following manuscript details our findings that maltol-derived oxidopyrylium ylides (i.e., with ortho methyl substitution relative to oxide) can be trapped prior to dimerization more efficiently than the regioisomeric allomaltol-derived ylide (i.e., with a para methyl substitution relative to oxide). Density functional theory studies provide evidence in support of a sterically (kinetically) controlled mechanism, whereby gauche interactions between appendages of the approaching maltol-derived ylides are privileged by higher barriers for dimerization and thus are readily intercepted by dipolarophiles via [5 + 2] cycloadditions. |
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AbstractList | Oxidopyrylium ylides are useful intermediates in synthetic organic chemistry because of their capability of forming structurally complex cycloadducts. They can also self-dimerize via [5 + 3] cycloaddition, which is an oft-reported side reaction that can negatively impact [5 + 2] cycloadduct yields and efficiency. In select instances, these dimers can be synthesized and used as the source of oxidopyrylium ylide, although the generality of this process remains unclear. Thus, how the substitution pattern governs both dimerization and cycloaddition reactions is of fundamental interest to probe factors to regulate them. The following manuscript details our findings that maltol-derived oxidopyrylium ylides (i.e., with ortho methyl substitution relative to oxide) can be trapped prior to dimerization more efficiently than the regioisomeric allomaltol-derived ylide (i.e., with a para methyl substitution relative to oxide). Density functional theory studies provide evidence in support of a sterically (kinetically) controlled mechanism, whereby gauche interactions between appendages of the approaching maltol-derived ylides are privileged by higher barriers for dimerization and thus are readily intercepted by dipolarophiles via [5 + 2] cycloadditions. Oxidopyrylium ylides are useful intermediates in synthetic organic chemistry because of their capability of forming structurally complex cycloadducts. They can also self-dimerize via [5 + 3] cycloaddition, which is an oft-reported side reaction that can negatively impact [5 + 2] cycloadduct yields and efficiency. In select instances, these dimers can be synthesized and used as the source of oxidopyrylium ylide, although the generality of this process remains unclear. Thus, how the substitution pattern governs both dimerization and cycloaddition reactions are of fundamental interest to probe factors to regulate them. The following manuscript details our findings that maltol-derived oxidopyrylium ylides ( i.e., with ortho methyl substitution relative to oxide) can be trapped prior to dimerization more efficiently than the regioisomeric allomaltol-derived ylide ( i.e., with an para methyl substitution relative to oxide). DFT studies provide evidence in support of a steric (kinetically) controlled mechanism, whereby gauche interactions between appendages of the approaching maltol-derived ylides are privileged by higher barriers for dimerization, and thus are readily intercepted by dipolarophiles via [5 + 2] cycloadditions. |
Author | Hersh, William H Garimallaprabhakaran, Aswin K Greer, Edyta M Greer, Alexander Murelli, Ryan P Suyabatmaz, Duygu M Bejcek, Lauren P |
AuthorAffiliation | Department of Chemistry PhD Program in Chemistry Department of Chemistry and Biochemistry The Graduate Center of the City University of New York Department of Natural Sciences |
AuthorAffiliation_xml | – name: The Graduate Center of the City University of New York – name: PhD Program in Chemistry – name: Department of Natural Sciences – name: Department of Chemistry – name: Department of Chemistry and Biochemistry – name: c Department of Natural Sciences, Baruch College, City University of New York, New York, NY, USA – name: d Department of Chemistry and Biochemistry, Queens College, City University of New York, Queens, NY, USA – name: a Department of Chemistry, Brooklyn College, The City University of New York, Brooklyn, NY, USA – name: b PhD Program in Chemistry, The Graduate Center of the City University of New York, New York, NY, USA |
Author_xml | – sequence: 1 givenname: Lauren P surname: Bejcek fullname: Bejcek, Lauren P organization: The Graduate Center of the City University of New York – sequence: 2 givenname: Aswin K surname: Garimallaprabhakaran fullname: Garimallaprabhakaran, Aswin K organization: Department of Chemistry – sequence: 3 givenname: Duygu M surname: Suyabatmaz fullname: Suyabatmaz, Duygu M organization: Department of Chemistry – sequence: 4 givenname: Alexander orcidid: 0000-0003-4444-9099 surname: Greer fullname: Greer, Alexander organization: The Graduate Center of the City University of New York – sequence: 5 givenname: William H orcidid: 0000-0002-9129-3464 surname: Hersh fullname: Hersh, William H organization: Department of Chemistry and Biochemistry – sequence: 6 givenname: Edyta M orcidid: 0000-0003-4283-0523 surname: Greer fullname: Greer, Edyta M email: edyta.greer@baruch.cuny.edu organization: Department of Natural Sciences – sequence: 7 givenname: Ryan P orcidid: 0000-0002-4247-3936 surname: Murelli fullname: Murelli, Ryan P email: rpmurelli@brooklyn.cuny.edu organization: The Graduate Center of the City University of New York |
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Snippet | Oxidopyrylium ylides are useful intermediates in synthetic organic chemistry because of their capability of forming structurally complex cycloadducts. They can... |
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SubjectTerms | Bridged Bicyclo Compounds - chemical synthesis Bridged Bicyclo Compounds - chemistry Chemistry Chemistry, Organic Cycloaddition Reaction Dimerization Kinetics Molecular Structure Physical Sciences Pyrones - chemistry Science & Technology Tropolone - chemical synthesis Tropolone - chemistry |
Title | Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5 + 3] Dimerization versus [5 + 2] Cycloaddition Reactions |
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