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T1 - Synthesis of Cyclic Guanidines via Silver-Catalyzed Intramolecular Alkene Hydroamination Reactions of N-Allylguanidines

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Amidines in Organic Synthesis ...............................

The contents include: Organic Synthesis: General Remarks; Stereoelectronic Effects and Reactivity; The Stability of Organic Compounds; Aliphatic Nucleophilic Substitutions: Problematic Electrophiles; The Alkylation of Carbanions; The Alkylation of Heteroatoms; The Acylation of Heteroatoms; Palladium Catalyzed C C Bond Formation; Cyclizations; and, Monofunctionalization of Symmetric Difunctional Substrates.

63 3.3 Application of Amidines to Organic Synthesis ...........
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Description :Guanidines, amidines and phosphazenes have been attracting attention in organic synthesis due to their potential functionality resulting from their extremely strong basicity. They are also promising c...

Guanidines in Organic Synthesis .............................

98 4.3 Guanidines as Synthetic Tools ..........................
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Ryan R. Walvoord was born in 1986 in the small town of Williamson, NY. He received a B.S. in Chemistry from the Rochester Institute of Technology in 2007, where he performed undergraduate research in the laboratories of Professor Christina G. Collison. In the same year, he began his graduate studies at the University of Pennsylvania under the guidance of Professor Marisa C. Kozlowski. His research in the Kozlowski group has focused on the synthesis and chemistry of arylnitromethanes, as well as the spectroscopic investigation of hydrogen bonding using colorimetric sensors.

Scott E. Allen was born in 1984 in Kutztown, Pennsylvania. He received his B.S. in chemistry from Penn State University, where he performed undergraduate research with Dr. Xumu Zhang. He then joined the laboratory of Dr. Marisa C. Kozlowski at the University of Pennsylvania, where his research focused on computational organic chemistry studies of N-heterocyclic carbene-catalyzed reactions in collaboration with Dr. Jeffery Bode at the ETH. Upon completion of his Ph.D. in early 2013, Scott joined the laboratory of Dr. Albert Bowers at the UNC Eshelman School of Pharmacy as a postdoctoral associate.

Application of Organosuperbases to Total Synthesis .........

295 10.2.1 Natural Amidines from Microorganisms and Fungi .........................................
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Because of their basicity and hydrogen-bonding properties, guanidines are an important functional group in many biologically active compounds of natural or synthetic origin. Consequently, methodologies for the parallel synthesis of guanidines have attracted much attention from both academia and industry. Numerous solid-phase routes have been reported, and the vast majority of these involve either urea or thiourea precursors or guanidine synthesis from pseudoureas or similarly activated amidines.

Contents: 1 Organic Synthesis: General Remarks 2 Stereoelectronic Effects and Reactivity 3 The Stability of Organic Compounds 4 Aliphatic Nucleophilic Substitutions: Problematic Electrophiles 5 The Alkylation of Carbanions 6 The Alkylation of Heteroatoms 7 The Acylation of Heteroatoms 8 Palladium-Catalyzed C-C Bond Formation 9 Cyclizations 10 Monofunctionalization of Symmetric Difunctional Substrates.

299 10.3.1 Natural Guanidines from Microorganisms ........
Photo provided by Flickr
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  • Solid phase synthesis of guanidines - ScienceDirect

    Many failures may, however, be avoided by understanding the structure-reactivity relationship of organic compounds.

  • Side Reactions in Organic Synthesis: A Guide to …

    Many failures may, however, be avoided by understanding the structure reactivity relationship of organic compounds.

  • Solid-phase organic synthesis (eBook, 2000) …

    Solid-phase organic synthesis

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Recent developments in combinatorial organic synthesis

Description :The individual chapters in this volume cover the scope and impact of main group organometallic compounds and reagents on organic synthesis during the last ten to fifteen years. In a number of chapters...

Superbases for Organic Synthesis, Tsutomu Ishikawa - …

Guanidines are categorized as strong organobases; however, their catalytic utility in organic synthesis has not been discussed thoroughly. The author's group has extensively and systematically studied their potential ability focusing on: 1) modified guanidines as chiral auxiliaries; 2) guanidinium ylides for aziridine formation; 3) the affinity of bisguanidine for proton and metal salts; and 4) the potential chirality of bisguanidine. Under the first topic, a variety of chiral guanidines was designed by the introduction of chirality on the three guanidinyl nitrogens, and the modified guanidines prepared using our original methods were found to be effective not only in catalytic but also in stoichiometric asymmetric syntheses. Under the second topic, the reaction of guanidinium salts carrying a glycinate function with aromatic or unsaturated aldehydes under basic conditions unexpectedly afforded aziridine-2-carboxylates, which were available as useful building blocks in organic synthesis due to their convertibility to functionalized amino acid derivatives in the ring-opening reaction, together with urea compounds recyclable to the starting guanidinium salts. The introduction of a chiral template to the guanidinium salt allowed us to expand the cyclic aziridination reaction to an asymmetric version. Under the third topic, effective complexabilty of bisguanidines with either proton or metal ions in water was observed, suggesting their possible application to the removal of toxic substances from polluted water and recovery of rare elements as material sources. Under the final topic, monomethylation or monoethylation of bisguanidine afforded a chiral product asymmetric crystallization, indicating that bisguanidines have a potential chiral character due to the plane asymmetry.

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