Title : Heteroatom influence on the pi-facial selectivity of Diels-Alder cycloadditions to 1-oxa-4-thia-6-vinylspiro[4.5]dec-6-ene, 3-methoxy-3-methyl-2-vinylcyclohexene, and 3-methoxy-2-vinylcyclohexene.

Pub. Date : 2002 Feb 22

PMID : 11846651






8 Functional Relationships(s)
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1 The addition of dimethylacetylene dicarboxylate (DMAD) is influenced by the electrostatic repulsion arising from the interaction of an electron pair orbital on the acetal oxygen and the orthogonal pi-orbital of the acetylene unit in DMAD in the syn-to-oxygen addition of the latter. Oxygen synemin Homo sapiens
2 The addition of dimethylacetylene dicarboxylate (DMAD) is influenced by the electrostatic repulsion arising from the interaction of an electron pair orbital on the acetal oxygen and the orthogonal pi-orbital of the acetylene unit in DMAD in the syn-to-oxygen addition of the latter. Oxygen synemin Homo sapiens
3 This repulsion is offset on coordination of Li+ to the said oxygen electron pair orbital, and the addition thus proceeds syn to oxygen. Oxygen synemin Homo sapiens
4 This repulsion is offset on coordination of Li+ to the said oxygen electron pair orbital, and the addition thus proceeds syn to oxygen. Oxygen synemin Homo sapiens
5 The enhanced and accelerated syn-to-oxygen addition in lithium perchlorate in nitromethane is interpreted as a consequence of the coordination of Li+ to both the acetal oxygen and a heteroatom in the dienophile that brings them in close proximity to facilitate a reaction. Oxygen synemin Homo sapiens
6 The enhanced and accelerated syn-to-oxygen addition in lithium perchlorate in nitromethane is interpreted as a consequence of the coordination of Li+ to both the acetal oxygen and a heteroatom in the dienophile that brings them in close proximity to facilitate a reaction. Oxygen synemin Homo sapiens
7 The Li+-oxygen combination, however, also exerts some steric effect that results in reduced syn-to-oxygen addition of dienophiles having large substituents such as N-phenylmaleimide. Oxygen synemin Homo sapiens
8 The Li+-oxygen combination, however, also exerts some steric effect that results in reduced syn-to-oxygen addition of dienophiles having large substituents such as N-phenylmaleimide. Oxygen synemin Homo sapiens