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Thursday, July 30, 2020 | History

2 edition of Ring opening reactions of oxabicyclic compounds found in the catalog.

Ring opening reactions of oxabicyclic compounds

Shihong Ma

Ring opening reactions of oxabicyclic compounds

formation of substituted cyclohexadienes, cyclohexenols and cycloheptenols.

by Shihong Ma

  • 267 Want to read
  • 40 Currently reading

Published .
Written in English


The Physical Object
Pagination257 leaves.
Number of Pages257
ID Numbers
Open LibraryOL17314376M
ISBN 100612188973

• An electrocyclic ring-opening reaction is a reaction in which a! bond of a cyclic reactant is cleaved to form a conjugated product with one more " bond. ∆ Cleave this σ bond. cyclobutene 1 π bond 1,3-butadiene 2 π bonds • A cycloaddition is a reaction between two compounds with " bonds to form a cyclic. Read "ChemInform Abstract: Ring Opening Reactions of Oxabicyclic Compounds as a Route to Cyclic and Acyclic Compounds with Multiple Stereocenters, ChemInform" on DeepDyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips.

If oxides have a lot of ring or angle strain, this makes them very reactive towards ring opening. So in this video, we'll look at the ring opening reactions of epoxides using strong nucleophiles. So in the first step, we add a strong nucleophile to our .   Read "ChemInform Abstract: Ring‐Opening Reactions of Oxabicyclic Alkene Compounds: Enantioselective Hydride and Ethyl Additions Catalyzed by Group 4 Metals., ChemInform" on DeepDyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips.

An electrocyclic reaction is the concerted cyclization of a conjugated π-electron system by converting one π-bond to a ring forming σ-bond. The reverse reaction may be called electrocyclic ring opening. Two examples are shown on the right. The electrocyclic ring closure is is designated by blue arrows, and the ring opening by red arrows.   Reaction mechanisms of ring-opening polymerization and structures and properties of resulting polymers of bicyclic acetals including 6,8-dioxabicyclo[]octane (abbreviated to DBO) and 6,8-dioxabicyclo[]octene (DBOE), bicyclic oxalactone 6,8-dioxabicyclo[]octanone (DBOO), bicyclic oxalactam 8-oxaazabicyclo[]octan


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Ring opening reactions of oxabicyclic compounds by Shihong Ma Download PDF EPUB FB2

The ring opening reaction of 8-oxabicyclo[]octenone 1, with cuprates is described.S N 2′ attack to give 3 is the predominant pathway giving rise to products isomeric to those derived from opening of vinyl epoxides under similar conditions, e.g.

by:   ChemInform Abstract: Ring-Opening Reactions of Oxabicyclic Alkene Compounds: Enantioselective Hydride and Ethyl Additions Catalyzed by Group 4 Metals.

ChemInform31 (44), no-no. DOI: /chin Richard D. Broene. Reductive Coupling of Unactivated Alkenes and by:   Chiu P., Lautens M. () Using ring-opening reactions of oxabicyclic compounds as a strategy in organic synthesis.

In: Metz P. (eds) Stereoselective Heterocyclic Synthesis II. Topics in Current Chemistry, vol Cited by: Request PDF | Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis | This chapter discusses the various methods for the preparation of oxabicyclic compounds.

In an effort to increase the rate of the reaction, excess magnesium bromide was added, the rationale being that the complexation of the Uwis acid Table Reductive Ring-Opening of Oxabicyclic Compounds Entry Oxabicyclic Compound Hydride Source' Product Yew O OTBDMS 1,e1:_-k~OTBDMS OTBDMS 1 OTBDMS A 2 OH 68% B 76% 2 O Cited by: A new efficient platinum-catalyzed ring-opening reaction of oxabicyclic alkenes with a wide range of sodium arylsulfinates was developed, affording the desired products 3 or 4 in good to excellent yields under mild conditions.

This protocol provides a new low-cost, viable and convenient method toward the synthesis of cisaryl-1,2-dihydronaphthalenols 3 and 2-aryl. An asymmetric ring‐opening reaction of aza/oxabicyclic alkenes with aromatic oximes was established.

The reaction was co‐catalyzed by Pd(OAc) 2 and zinc triflate with (R)‐DIFLUORPHOS as the chiral ligand, affording cis‐stereoselective asymmetric ring‐opening products. A synthetic application of this method has been demonstrated by transforming the. Title: The Ring Opening of Oxabicyclic Compounds Controlled by a Phenylsulfonyl Group.

Synthetic Applications. VOLUME: 6 ISSUE: 7 Author(s):Odon Arjona and Joaquin Plumet Affiliation:Universidad ad de amento de Quimica Orgánica Keywords:oxabicyclic compound, oxabicyclic derivative. The ring opening of oxabicyclic compounds with a variety of nucleophiles can serve as a useful reaction for the synthesis of cyclic and acyclic compounds with multiple stereocenters.

Highly regio- and stereoselective reactions have been observed with organocuprates, silylcuprates, organolithium reagents and organomagnesium compounds.

An application of various oximes as nucleophiles in the asymmetric ring‐opening (ARO) reaction of aza/oxabicyclic alkenes resulting in cis‐ARO products has been reaction was co‐catalyzed by Pd(OAc) 2 and Zn(OTf) 2 with (R)‐DIFLUORPHOS as the chiral methodology exhibits broad substrate scope, functional group tolerance with high.

The formation of the 1,2-trans products is atypical for ring opening reactions of oxabicyclic alkenes, which usually generate the syn-1,2 diastereomers via exo nucleophilic attack (1, 2).

Furthermore, regio- and stereochemical results diverge from previously documented rhodium-catalyzed reactions with allylic carbonates (9 – 18).

In polymer chemistry, ring-opening polymerization (ROP) is a form of chain-growth polymerization, in which the terminus of a polymer chain attacks cyclic monomers to form a longer polymer (see figure).

The reactive center can be radical, anionic or cyclic monomers such as norbornene or cyclooctadiene can be polymerized to high molecular. The mechanism of an asymmetric ring-opening (ARO) addition of oxabicyclic alkenes catalyzed by a platinum(II) catalyst was investigated by MX/G(d,p) using density functional theory (DFT).All the structures were optimized in the solvent model density (SMD) solvation model (solvation = the mixture of H 2 O/CH 2 Cl 2 1: 10, v/v) for consistence with experimental.

Title: Ring-Opening Reactions of Oxabicyclic Alkene Compounds: Enantioselective Hydride and Ethyl Additions Catalyzed by Group 4 Metals: Publication Type. Zirconium catalysts catalyze the ring-opening of [] 2, 4-dimethyl(benzyloxy)oxabicyclooctene (7) when ethylmagnesium bromide is used as a reagent.

Both hydride and ethyl addition products are obtained at all conditions studied. A new efficient platinum-catalyzed ring-opening reactions of oxabicyclic alkenes with a wide range of sodium arylsulfinates was developed, affording the desired products 3 or 4 in good to.

Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time.

The reaction gave the corresponding trans -1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of mol % [Ir(COD)Cl] 2 and 5 mol.

Ring-opening reaction with hydride Conclusion Although great optimization is still required, we have developed the first example of ring-opening reaction of an oxabicyclic alkene with hydride. The methodology was useful to access 1,2-dihydronaphthalene and its ring contraction by iodine(III) gave an indane.

Acknowledgements. D Ring-Opening Reactions of Oxacyclopropanes. Unlike most ethers, oxacyclopropanes react readily with nucleophilic reagents. These reactions are no different from the nucleophilic displacements previously encountered in Chapter 8, except that the leaving group, which is the oxygen of the oxide ring, remains a part of the original molecule.

Generally, some transition metals, such as rhodium, copper as well as palladium, have been commonly employed for this type nucleophilic ring opening reactions 8,9,10, Lautens reported in that rhodium/Josiphos catalyzed the asymmetric ring-opening (ARO) reaction of oxabicyclic alkenes involving heteroatom nucleophiles 8.

Ring opening of oxetanes can be carried out under a variety of reaction conditions. In this review article, an up-to-date overview of major synthetic methodologies involved in the ring opening of oxetanes as well as their synthetic applications has been presented.A cyclic compound (ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both .Electrocyclic Reactions!

Ring constraints can impact rates of normal electrocyclic ring opening reactions! Consider a cyclobutene ring opening when included in a bicyclic compound! 4 e’s, therefore CON!

H H Would generate a trans double bond, but ring is 10 carbons, so Bredt’s rule is not violated! ˚C! H H Ring is 3 carbons shorter!