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Friday, July 24, 2020 | History

2 edition of 3-sulfinylthiochromin-4-one and its Diels-Alder reactions with electron-rich dienophiles. found in the catalog.

3-sulfinylthiochromin-4-one and its Diels-Alder reactions with electron-rich dienophiles.

Donna Kaye T.* Hutchinson

3-sulfinylthiochromin-4-one and its Diels-Alder reactions with electron-rich dienophiles.

by Donna Kaye T.* Hutchinson

  • 135 Want to read
  • 23 Currently reading

Published .
Written in English


The Physical Object
Pagination67 leaves
Number of Pages67
ID Numbers
Open LibraryOL20724331M

The paper describes the course of cycloadditions of Diels-Alder dienophiles containing linked enyne sites, each substituted with activating groups. Consistently, it was found that in the enyne cases the Diels-Alder reaction occurred specifically at the acetylenic center. Despite the poor reputation of electron-deficient pyridazines in intermolecular Hetero Diels-Alder (HDA) reactions, 4,5-dicyanopyridazine (DCP) showed a surprising reactivity as a heterocyclic azadiene in inverse electron-demand HDA processes with different dienophiles. The use of alkenes, alkynes and enamines as 2p electron counterparts afforded dicyanocyclohexa-1,3-dienes and substituted Cited by: 8.

  [reaction: see text] Ultrahigh pressures and catalytic Yb(OTf)(3).2H(2)O were found to mediate Diels-Alder reactions of various electron-deficient dienophiles with 1,3-cyclohexadiene to produce endo-bicyclo[ 2]octenes in moderate to excellent yield and selectivity. The proposed total synthesis of hapalindole Q based on bicyclo[ 2]oct Cited by: An inverse demand Diels-Alder reaction takes place between an electron deficient conjugated diene and electron rich dienophile to give cyclic adducts. To give: The products of the inverse-demand Diels-Alder reaction shown with their correct stereochemistry. Further if more than one regioisomer is possible then to give their structures.

Diels-Alder reactions of 5-nitroquinoline with 6,7 and 8. The reactions of 5-nitroquinoline with these dienes, yield the same products that using [HMIM][BF 4] as solvent but with lower yield. In the cases of dienes 7 and 8 the normal addition products 34 respectively, show complete aromatization due to the loss of the nitro and Cited by: 1. The Diels-Alder reaction is a [4+2] cycloaddition, forming three bonds in one step and closing a ring in the process. Examine the electron flow in the diagram below. The electron rich diene reactions with the 1,4-benzoquinone in a [4+2] cycloaddition. The result is a fused ring system with two fewer alkenes than the combined starting materials%(5).


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3-sulfinylthiochromin-4-one and its Diels-Alder reactions with electron-rich dienophiles by Donna Kaye T.* Hutchinson Download PDF EPUB FB2

The Diels–Alder reaction is a well-known and established reaction in organic chemistry consisting of a highly selective [4+2] cycloaddition of a diene to an alkene (dienophile) to yield cyclohexene derivatives (Scheme A).This reaction provides an opportunity to surpass the limitations related to the coupling of chemically sensitive (bio)molecules (as antibodies), especially in aqueous.

How to Cite. Rickborn, B. The Retro–Diels–Alder Reaction Part II. Dienophiles with One or More Heteroatom. Organic Reactions. – Diels-Alder ligation of electron-rich hexadiene and electron-deficient maleimide has been found to be facilitated by electron withdrawing groups (e.g., C = O and C ≡ N) on the dienophile and.

Since its discovery inthe Diels-Alder reaction has evolved as one of the most important reactions for accessing complex six-membered ring derivatives due to high functional group tolerance Author: Johan Franzén.

reactive dienophiles, forming cycloadducts with a wide variety of 1,3-dienes. Unactivated (N,C-alkyl/aryl-substituted) and electron-rich (heteroatom-substituted) imino dienophiles can also undergo ImDA reactions with highly reactive electron-rich dienes or under Lewis or protic acid catalysis.

Dipak K. Mandal, in Pericyclic Chemistry, Regioselectivity of Hetero Diels–Alder Reactions. Hetero Diels–Alder reactions involve a heterodiene or a heterodienophile where the heteroatom is a part of the π system (see Fig.

).Here the two σ bonds being formed in the transition structure are usually different, C C and C X (X is a heteroatom). Design of Chiral N-Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and Its Application to Asymmetric Diels-Alder Reaction D.

Nakashima, H. Yamamoto, J. Chem. Soc., A Mild and Efficient Asymmetric Hetero-Diels-Alder Reaction of. core this question 1 out o ure" button to launch the drawing utility.

triple bonds are also Diels-Alder dienophiles. With this e following reaction + CH,O,C-C-C-CO,CH3 Get more help from Chegg. Title: The Retro-Diels-Alder Reaction. Part II. Dienophiles with One or More Heteroatoms: Author(s) Rickborn, Bruce: Volume: Year of Publication: Author(s): Rickborn, Bruce.

DIELS- ALDER REACTION 1. DIELS-ALDER REACTION VIPUL BATRA 1 + O 91% O O O O O O 2. INTRODUCTION In the Diels-Alder reaction, a 1,3 diene reacts with a dienophile to form a six membered ring adduct.

Two new σ bonds and a new ∏ bond are formed at the expense of three ∏ bonds in the starting materials. The regioselective inverse electron demand Diels−Alder reactions of 6-[(tert-butyloxycarbonyl)amino](methylthio)-1,2,4,5-tetrazine (2), 6-(acetylamino)(methylthio)-1,2,4,5-tetrazine (3), and 6-(benzyloxycarbonyl)amino(methylthio)-1,2,4,5-tetrazine (4) are disclosed.

All three underwent regioselective [4 + 2] cycloaddition with electron-rich dienophiles to form the corresponding Cited by: The Inverse electron demand Diels–Alder reaction, or DA INV or IEDDA is an organic chemical reaction, in which two new chemical bonds and a six-membered ring are formed.

It is related to the Diels–Alder reaction, but unlike the Diels–Alder (or DA) reaction, the DA INV is a cycloaddition between an electron-rich dienophile and an electron-poor diene.

In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile (also spelled dieneophile), to form a substituted cyclohexene derivative.

It is the prototypical example of a pericyclic reaction with a concerted specifically, it is classified as a thermally-allowed [4+2] cycloaddition with Organic Chemistry Portal: diels-alder-reaction.

The reactions performed in water occurred in heterogeneous phase but were faster than those executed in toluene or dichloroethane (DCE). 1a−c, 5, and 6 behaved as 2π components in the Diels−Alder cycloadditions with 7−10 and exo adducts were preferentially or exclusively by: Diels–Alder reaction explained.

In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile (also spelled dieneophile), to form a substituted cyclohexene derivative.

It is the prototypical example of a pericyclic reaction with a concerted specifically, it is classified as a. Discrete Macromolecular Constructs via the Diels–Alder ‘‘Click’’ Reaction Gurkan Hizal,1 Umit Tunca,1 Amitav Sanyal2 1Department of Chemistry, Istanbul Technical University, MaslakIstanbul, Turkey 2Department of Chemistry, Bogazici University, BebekIstanbul, Turkey Correspondence to: A.

Sanyal (E-mail: @), U. Tunca (E-mail: [email protected] Cited by: This banner text can have markup. web; books; video; audio; software; images; Toggle navigation.

Highly Selective Diels-Alder Reactions of Directly Connected Enyne Dienophiles Mingji Dai, David Sarlah, Maolin Yu, Samuel J.

Danishefsky,* Gavin O. Jones and K. Houk *The Sloan-Kettering Institute for Cancer Research Center, York Avenue, Room RRLNew York, New YorkEmail: s-danishefsky Abstract: The mechanism, potential energy surface, substituent effect and salvation effect of two types of Diels-Alder reactions between silabenzenes and some dienophiles were investigated using density functional theory (DFT) at B3LYP/G(d,p) level.

All the studied reactions proceeded in a concerted way. The influence of phenyl at the C atom of dienophiles on the asynchronicity in the. I discuss the aqueous Diels-Alder reaction in Chapter of my book.

A key case is the reaction of methyl vinyl ketone with cyclopentadiene, Reaction 1. The reaction is accelerated by a factor of in water over the rate in isooctane. 1 Jorgensen argues that this acceleration is due to stronger hydrogen bonding to the ketone than in the.

A theoretical study of the regioselectivity of the Diels-Alder reaction between 1,8-dichloroanthracene and acrolein is performed using DFT at the B3LYP/G(d,p) level of theory. The FMO analysis, global and local reactivity indices confirmed the reported experimental results.

Potential energy surface analysis showed that the cycloadditions (CAs) favor the formation of the anti : Mujeeb A. Sultan, Usama Karama, Abdulrahman I.

Almansour, Saied M. Soliman.1 Introduction Diels–Alder (DA) reaction is one of the most common reactions used in organic chemistry and invented by Otto Diels and Kurt Alder who received the Nobel Prize in for their discovery. 1 DA reaction involves a straightforward [4 + 2] cycloaddition reaction between an electron-rich diene (furan and its derivatives, 1,3 cyclopentadiene and its derivatives, etc.) and an Cited by: The reaction between N-acylamino(methylthio)-1,2,4,5-tetranizes 1 with electron-rich dienophiles 2 gives the corresponding 1,2-diazines 3 in excellent yields and with high regioselectivity (Scheme ).Author: Mar Gómez Gallego, Miguel A.

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