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Compounds 1-3, called alkenyl phosphates, were investigated as electrophiles in Negishi coupling reactions with organozinc compounds 4 and 5. The phosphate group, -OP(=O)(OPh) 2, serves as the leaving group in the reaction. Draw the structures of the products from each of the following combinations of reactants in the presence of a Pd catalyst: •Oloto. OPh + OPh (a) (1 equivalent) (1 equivalent) ZnBr

Compounds 1-3, called alkenyl phosphates, were investigated as electrophiles in Negishi coupling reactions with organozinc compounds 4 and 5. The phosphate group, -OP(=O)(OPh) 2, serves as the leaving group in the reaction. Draw the structures of the products from each of the following combinations of reactants in the presence of a Pd catalyst: •Oloto. OPh + OPh (a) (1 equivalent) (1 equivalent) ZnBr

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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**Compounds 1–3 as Electrophiles in Negishi Coupling Reactions** In this study, compounds 1–3, known as alkenyl phosphates, are examined for their reactivity as electrophiles in Negishi coupling reactions with organozinc compounds 4 and 5. The phosphate group, –OP(=O)(OPh)₂, functions as the leaving group in the reactions. The task is to draw the structures of the products resulting from each combination of reactants in the presence of a palladium (Pd) catalyst. **Reaction Example (a):** - **Reactants:** - A cyclohexyl alkenyl phosphate (structure shown) with a phosphate leaving group. - An organozinc compound with a ZnBr group attached to a five-membered ring. Both reactants are present in equimolar amounts (1 equivalent each). To complete the exercise, draw the solution indicating the resulting product from this reaction given the conditions and reactants. Use the "Draw Your Solution" tool provided to illustrate the chemical structure. This investigation highlights the role of alkenyl phosphates in forming carbon-carbon bonds through catalytic processes, an important methodology in synthetic organic chemistry.
Transcribed Image Text:**Compounds 1–3 as Electrophiles in Negishi Coupling Reactions** In this study, compounds 1–3, known as alkenyl phosphates, are examined for their reactivity as electrophiles in Negishi coupling reactions with organozinc compounds 4 and 5. The phosphate group, –OP(=O)(OPh)₂, functions as the leaving group in the reactions. The task is to draw the structures of the products resulting from each combination of reactants in the presence of a palladium (Pd) catalyst. **Reaction Example (a):** - **Reactants:** - A cyclohexyl alkenyl phosphate (structure shown) with a phosphate leaving group. - An organozinc compound with a ZnBr group attached to a five-membered ring. Both reactants are present in equimolar amounts (1 equivalent each). To complete the exercise, draw the solution indicating the resulting product from this reaction given the conditions and reactants. Use the "Draw Your Solution" tool provided to illustrate the chemical structure. This investigation highlights the role of alkenyl phosphates in forming carbon-carbon bonds through catalytic processes, an important methodology in synthetic organic chemistry.
### Chemical Reaction Simulation #### Reaction (b) - **Reactant 1:** - Structure: Cyclohexane ring attached to a phosphoric acid diester (two phenyl groups attached to phosphorus) - Quantity: 1 equivalent - **Reactant 2:** - Structure: A linear chain with a nitrile group (NC) attached to an alkyl group, ending with a zinc bromide (ZnBr) moiety - Quantity: 1 equivalent - **Instruction:** Draw your solution for the given reaction using interactive tools. #### Reaction (c) - **Reactant 1:** - Structure: Aromatic ring with two methoxy groups (OMe) and a phosphoric acid diester (two phenyl groups attached to phosphorus) - Quantity: 1 equivalent - **Reactant 2:** - Structure: A three-membered ring with an ether linkage and a zinc bromide (ZnBr) moiety - Quantity: 1 equivalent - **Instruction:** Similarly, use interactive tools to draw the resulting compound of the reaction. ### Diagrams Both sections include molecular structures that need to be analyzed to predict the outcomes of their respective chemical reactions. Use the tools provided to visualize and sketch potential products.
Transcribed Image Text:### Chemical Reaction Simulation #### Reaction (b) - **Reactant 1:** - Structure: Cyclohexane ring attached to a phosphoric acid diester (two phenyl groups attached to phosphorus) - Quantity: 1 equivalent - **Reactant 2:** - Structure: A linear chain with a nitrile group (NC) attached to an alkyl group, ending with a zinc bromide (ZnBr) moiety - Quantity: 1 equivalent - **Instruction:** Draw your solution for the given reaction using interactive tools. #### Reaction (c) - **Reactant 1:** - Structure: Aromatic ring with two methoxy groups (OMe) and a phosphoric acid diester (two phenyl groups attached to phosphorus) - Quantity: 1 equivalent - **Reactant 2:** - Structure: A three-membered ring with an ether linkage and a zinc bromide (ZnBr) moiety - Quantity: 1 equivalent - **Instruction:** Similarly, use interactive tools to draw the resulting compound of the reaction. ### Diagrams Both sections include molecular structures that need to be analyzed to predict the outcomes of their respective chemical reactions. Use the tools provided to visualize and sketch potential products.
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