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- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/19%3A_Aldehydes_and_Ketones-_Nucleophilic_Addition_Reactions/19.11%3A_Nucleophilic_Addition_of_Phosphorus_Ylides_-_The_Wittig_ReactionThe initial mechanistic step to form the oxaphosphetane intermediate appears to take place by different pathways which is dependent on the structure of the reactants and the exact experimental conditi...The initial mechanistic step to form the oxaphosphetane intermediate appears to take place by different pathways which is dependent on the structure of the reactants and the exact experimental conditions. A principal advantage of alkene synthesis by the Wittig reaction is that the location of the double bond is absolutely fixed, in contrast to the mixtures often produced by alcohol dehydration or other elimination reactions.
- https://chem.libretexts.org/Bookshelves/General_Chemistry/Book%3A_Structure_and_Reactivity_in_Organic_Biological_and_Inorganic_Chemistry_(Schaller)/III%3A_Reactivity_in_Organic_Biological_and_Inorganic_Chemistry_1/03%3A_Addition_to_Carbonyls/3.13%3A_Addition_of_YlidesIn the product, box the part of the structure that came from the compound on the left; circle the new part. Based on the superior activity of the analog, the active conformation of the ring is probabl...In the product, box the part of the structure that came from the compound on the left; circle the new part. Based on the superior activity of the analog, the active conformation of the ring is probably more like the one on the right than the one on the left. The circled bond probably adopts a dihedral angle closer to 180 degrees, with the rest of the ring twisting into a shape more like the one shown on the right, in order to bind to the target.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/19%3A_Aldehydes_and_Ketones-_Nucleophilic_Addition_Reactions/19.11%3A_Nucleophilic_Addition_of_Phosphorus_Ylides_-_The_Wittig_ReactionThe initial mechanistic step to form the oxaphosphetane intermediate appears to take place by different pathways which is dependent on the structure of the reactants and the exact experimental conditi...The initial mechanistic step to form the oxaphosphetane intermediate appears to take place by different pathways which is dependent on the structure of the reactants and the exact experimental conditions. A principal advantage of alkene synthesis by the Wittig reaction is that the location of the double bond is absolutely fixed, in contrast to the mixtures often produced by alcohol dehydration or other elimination reactions.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/05%3A_Aldehydes_and_Ketones-_Nucleophilic_Addition_Reactions/5.09%3A_Nucleophilic_Addition_of_Phosphorus_Ylides_-_The_Wittig_ReactionThe initial mechanistic step to form the oxaphosphetane intermediate appears to take place by different pathways which is dependent on the structure of the reactants and the exact experimental conditi...The initial mechanistic step to form the oxaphosphetane intermediate appears to take place by different pathways which is dependent on the structure of the reactants and the exact experimental conditions. A principal advantage of alkene synthesis by the Wittig reaction is that the location of the double bond is absolutely fixed, in contrast to the mixtures often produced by alcohol dehydration or other elimination reactions.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Organo-phosphorus_Compounds/Reactivity_of_Phosphorus_Compounds/Reactions_of_YlidesA principal advantage of alkene synthesis by the Wittig reaction is that the location of the double bond is absolutely fixed, in contrast to the mixtures often produced by alcohol dehydration. Because...A principal advantage of alkene synthesis by the Wittig reaction is that the location of the double bond is absolutely fixed, in contrast to the mixtures often produced by alcohol dehydration. Because of the additional allylic stabilization of the ylide group, the new double bonds (colored blue) have an E-configuration, in contrast to the Z-configuration favored by unstabilized ylides (equation 2).
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/16%3A_Carbonyl_Compounds_I-_Aldehydes_and_Ketones._Addition_Reactions_of_the_Carbonyl_Group/16.05%3A_Typical_Carbonyl-Addition_ReactionsWe turn now to discuss a few specific addition reactions of the carbonyl groups of aldehydes and ketones. We shall not attempt to provide an extensive catalog of reactions, but will try to emphasize t...We turn now to discuss a few specific addition reactions of the carbonyl groups of aldehydes and ketones. We shall not attempt to provide an extensive catalog of reactions, but will try to emphasize the principles involved with especially important reactions that are useful in synthesis.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/19%3A_Aldehydes_and_Ketones-_Nucleophilic_Addition_Reactions/19.11%3A_Nucleophilic_Addition_of_Phosphorus_Ylides-_The_Wittig_ReactionAldehydes and ketones are converted into alkenes by means of a nucleophilic addition called the Wittig reaction, after the German chemist Georg Wittig who won the 1979 Nobel Prize in Chemistry. The re...Aldehydes and ketones are converted into alkenes by means of a nucleophilic addition called the Wittig reaction, after the German chemist Georg Wittig who won the 1979 Nobel Prize in Chemistry. The reaction has no direct biological counterpart but is important both because of its wide use in drug manufacture and because of its mechanistic similarity to reactions of the coenzyme thiamin diphosphate.
- https://chem.libretexts.org/Ancillary_Materials/Reference/Organic_Chemistry_Glossary/YlideA ylide is a neutral species in which there is a carbon atom bearing a formal charge of -1 bound to a heteroatom bearing a formal charge of +1. Ylides are classified based on the nature of the positi...A ylide is a neutral species in which there is a carbon atom bearing a formal charge of -1 bound to a heteroatom bearing a formal charge of +1. Ylides are classified based on the nature of the positively charged heteroatom.
