Optimization of Grignard Addition to Esters: Kinetic and Mechanistic Study of Model Phthalide Using Flow Chemistry

Optimization of Grignard Addition to Esters: Kinetic and Mechanistic Study of Model Phthalide Using Flow Chemistry

© 2018 American Chemical Society. The kinetics of sequential addition of a distinct Grignard species onto a lactone is studied by flow chemistry. The experimental data are shown to be consistent with a kinetic model based on four reaction steps, reaction of ester to magnesium hemiacetal, rearrangeme...

Descrizione completa

Dettagli Bibliografici
Autori principali:	Pedersen, Michael J, Born, Stephen, Neuenschwander, Ulrich, Skovby, Tommy, Mealy, Michael J, Kiil, Søren, Dam-Johansen, Kim, Jensen, Klavs F
Altri autori:	Massachusetts Institute of Technology. Department of Chemical Engineering
Natura:	Articolo
Lingua:	English
Pubblicazione:	American Chemical Society (ACS) 2021
Accesso online:	https://hdl.handle.net/1721.1/135019

Documenti analoghi

Catalytic intramolecular ketone hydroacylation: enantioselective synthesis of phthalides.
di: Willis, M
Pubblicazione: (2010)

Olefin Autoxidation in Flow
di: Neuenschwander, Ulrich, et al.
Pubblicazione: (2015)

A Clock Reaction Based on Molybdenum Blue
di: Neuenschwander, Ulrich, et al.
Pubblicazione: (2015)

STEREOCHEMICAL AND MECHANISTIC ASPECTS OF THE NICKEL-COMPLEX CATALYZED FORMATION OF OLEFINS FROM ALLYLIC ALCOHOLS AND GRIGNARD-REAGENTS
di: Felkin, H, et al.
Pubblicazione: (1981)

Grignard preparation of benzoic acid [slaid]
Pubblicazione: (1978)

Mechanistic organometallic chemistry
di: Brown, S, et al.
Pubblicazione: (1986)

Preparation and reactions of medium-ring Grignard reagent
di: Fleckenstein, Lee Joseph, 1930-
Pubblicazione: (2024)

Asymmetric conjugate addition of grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes
di: Zhao, Kai, et al.
Pubblicazione: (2015)

Investigations of the di-grignard approach to four membered metallacycles
di: , BOER, Henricus Jacobus Robert de, et al.
Pubblicazione: (1989)

Continuous manufacturing – the Green Chemistry promise?
di: Rogers, Luke, et al.
Pubblicazione: (2020)

A mechanistic approach to organic chemistry/
di: Thomas, Gareth, 1932-
Pubblicazione: (1967)

EPOXIDE OPENING WITH ORGANOCUPRATES AND GRIGNARD-REAGENTS IN THE PRESENCE OF CHIRAL LIGANDS
di: Davies, S, et al.
Pubblicazione: (1980)

Oscillatory multiphase flow strategy for chemistry and biology
di: Abolhasani, Milad, et al.
Pubblicazione: (2017)

The role of flow in green chemistry and engineering
di: Newman, Stephen G., et al.
Pubblicazione: (2014)

The Use Of Grignard Reagent In Pheromone Synthesis For Palm Weevil (Rhynchorus, Sp) = Penggunaan Reagen Grignard Dalam Sintesis Feromon Kumbang Kelapa Indonesia, Rhynchorus Sp.
di: Perpustakaan UGM, i-lib
Pubblicazione: (2003)

Mechanistic Investigations of Epoxide Aminolysis in Microreactors at High Temperatures and Pressures
di: Zaborenko, Nikolay, et al.
Pubblicazione: (2013)

Terminal Aziridines by Addition of Grignard Reagents or Organoceriums to an (alpha-Chloro)sulfinylimine
di: Hodgson, D, et al.
Pubblicazione: (2009)

Copper-catalyzed asymmetric allylic substitution reactions with organozinc and Grignard reagents
di: Geurts, K, et al.
Pubblicazione: (2008)

Tertiary amine synthesis via reductive coupling of amides with Grignard reagents
di: Xie, L, et al.
Pubblicazione: (2017)

Cobalt-Catalyzed, Imine-Directed Olefin Hydroarylation under Grignard-Free Conditions
di: Xu, Wengang, et al.
Pubblicazione: (2017)

Reactions of a phosphavinyl Grignard reagent with main group mono-halide compounds
di: Aldridge, S, et al.
Pubblicazione: (2003)

Synthetic and mechanistic investigations of the aldehyde addition reactions of tartrate ester modified allylboronates
di: Hoong, Lee Keem, 1962-
Pubblicazione: (2005)

Phenanthrene synthesis via chromium-catalyzed annulation of 2-biaryl grignard reagents and alkynes
di: Yan, Jianming, et al.
Pubblicazione: (2019)

Development of Barbier-Grignard-type alkylation reaction using unactivated alkyl halides in water.
di: Shen, Zhi Liang.
Pubblicazione: (2008)

The reactivity of epoxides with lithium 2,2,6,6-tetramethylpiperidide in combination with organolithiums or grignard reagents.
di: Hodgson, D, et al.
Pubblicazione: (2007)

INORGANIC GRIGNARD-REAGENTS - PREPARATIONS AND REACTIONS OF [BROMOBIS-(TETRAHYDROFURAN)MAGNESIO]BIS(ETA-CYCLOPENTADIENYL)HYDRIDOMOLYBDENUM
di: Davies, S, et al.
Pubblicazione: (1978)

Cobalt-catalyzed multi-substituted alkene synthesis from 1,3-dithiolanes and Grignard reagents
di: Davidson, TAA, et al.
Pubblicazione: (2023)

ASYMMETRIC-SYNTHESIS IN THE NICKEL-COMPLEX-CATALYZED FORMATION OF OLEFINS FROM ALLYL ALCOHOLS AND GRIGNARD-REAGENTS
di: Cherest, M, et al.
Pubblicazione: (1981)

Alkenes from terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide and organolithiums or grignard reagents.
di: Hodgson, D, et al.
Pubblicazione: (2004)

Photochemical Synthesis of the Bioactive Fragment of Salbutamol and Derivatives in a Self‐Optimizing Flow Chemistry Platform
di: Gérardy, Romaric, et al.
Pubblicazione: (2022)

Cationic terminal borylene complexes: a synthetic and mechanistic investigation of M=B metathesis chemistry.
di: Kays, D, et al.
Pubblicazione: (2005)

INORGANO-GRIGNARD REAGENTS - PREPARATION, REACTIONS, AND X-RAY CRYSTAL-STRUCTURE OF BIS-(ETA-CYCLOPENTADIENYL)HYDRIDOMOLYBDENUM[BROMO-(BISTETRAHYDROFURAN)MAGNESIUM]
di: Davies, S, et al.
Pubblicazione: (1977)

Copper-catalyzed enantioselective conjugate addition of grignard reagents to methyl 4,4,4-trifluorocrotonate : synthesis of enantioenriched trifluoromethylated compounds
di: Zhang, Li-Ying, et al.
Pubblicazione: (2015)

Efficient kinetic experiments in continuous flow microreactors
di: Aroh, Kosi C., et al.
Pubblicazione: (2018)

Kinetic and mechanistic study of the methane coupling reaction
di: Burch, R, et al.
Pubblicazione: (1990)

KINETIC AND MECHANISTIC STUDY OF THE METHANE COUPLING REACTION
di: Burch, R, et al.
Pubblicazione: (1990)

Forces on underwater vehicles
di: Jensen, Søren Trøjgård
Pubblicazione: (2007)

“Batch” Kinetics in Flow: Online IR Analysis and Continuous Control
di: Moore , Jason Stuart, et al.
Pubblicazione: (2015)

Introduction to computational chemistry /
di: 290797 Jensen, Frank
Pubblicazione: (2007)

Catalytic enantioselective conjugate addition of grignard reagents to cyclic enones using C 1 -1,1′-bisisoquinoline-based chiral ligands
di: Judeh, Zaher M. A., et al.
Pubblicazione: (2013)