Steven Chung

Iowa State University

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Charles P. Casey

University of Wisconsin–Madison

Kirk Arvidson

United States Food and Drug Administration

Kevin D. Revell

Murray State University

Douglas R. Powell

University of Oklahoma

Huiyan Zhao

Iowa State University

Jason M. Ochaoda

Iowa State University

Walter S. Trahanovsky

Iowa State University

Synthia Chang

Iowa State University

Matthew Wells

Federal Reserve Bank of Richmond

Alexandra S. Goldstein

Harvey Mudd College

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Harvey Mudd College

Iowa State University

University of Wisconsin–Madison

Ames National Laboratory

Chinese Academy of Sciences

Tsinghua University

Harbin Institute of Technology

Jiangsu University

Xi'an Jiaotong University

University of Kansas

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Kinetic Addition of Nucleophiles to η³-Propargyl Rhenium Complexes Occurs at the Central Carbon to Produce Rhenacyclobutenes

Journal of the American Chemical Society (1998)

Charles P. Casey John R. Nash Chae S. Yi Anthony D. Selmeczy Steven Chung

Kinetic addition of nucleophiles occurs at the center carbon of η3-propargyl rhenium complexes to produce rhenacyclobutenes. Reaction of P(CH3)3 with C5Me5(CO)2Re[η3-CH2C⋮CC(CH3)3]+BF4- (3a) gave the metallacyclobutene C5Me5(CO)2ReCH2C(PMe3)CC(CH3)3+BF4- (4a), which was characterized by X-ray crystallography. Malonate and acetylide nucleophiles reacted with C5Me5(CO)2Re[η3-CH2C⋮CCH3]+PF6- (3b) to give metallacyclobutene complexes. Pyridine added to the central propargyl carbon of 3b at low temperature to produce the metastable metallacyclobutene C5Me5(CO)2ReCH2C(NC5H5)CCH3+PF6- (14b) which rearranged to the η2-allene complex C5Me5(CO)2Re[η2-H2CCC(NC5H5)CH3]+PF6- (15K) at room temperature. 4-(Dimethylamino)pyridine (DMAP) added to the central carbon of the tert-butyl-substituted η3-propargyl complex 3a below −38 °C to give the rhenacyclobutene complex C5Me5(CO)2ReCH2C(NC5H4NMe2)CC(CH3)3+BF4- (22a) which rearranged to the η2-alkyne complex C5Me5(CO)2Re[η2-(CH3)3CC⋮CCH2NC5H4NMe2]+BF4- (23) at room temperature. Reaction of water with C5Me5(CO)2Re[η3-CH2C⋮CH]+BF4- (3c) gave the hydroxyallyl complex C5Me5(CO)2Re[η3-CH2C(OH)CH2]+BF4- (29) by a process proposed to involve nucleophilic addition of water to the central propargyl carbon of 3c followed by protonation of the metallacyclobutene intermediate.

Propargyl

Alkyne

Allene

Acetylide

Nucleophilic Addition

10.1021/ja9729847

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Citations (61)

A Convenient Procedure for the Preparation of Levoglucosenone and Its Conversion to Novel Chiral Derivatives

ACS symposium series (2002)

Walter S. Trahanovsky Jason M. Ochaoda Chen Wang Kevin D. Revell Kirk Arvidson

As part of a study to develop methods to obtain high-value nonracemic chiral compounds from biomass, we have developed a convenient method for converting cellulose to levoglucosenone in >10% yield. This procedure and methods to convert levoglucosenone into potentially useful chiral derivatives are presented.

10.1021/bk-2003-0841.ch002

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Citations (8)

Preparation of conjugated soybean oil and other natural oils and fatty acids by homogeneous transition metal catalysis

Journal of the American Oil Chemists Society (2001)

Richard C. Larock Xiaoyang Dong Steven Chung Ch. Kishan Reddy Laurie E. Ehlers

Abstract The use of as little as 0.1 mol% [RhCl(C 8 H 14 ) 2 ] 2 , 0.25 mol% PtCl 2 (PPh 3 ) 2 , or 0.5 mol% RuHCl(CO)(PPh 3 ) 3 , where Ph = phenyl, catalyzes the isomerization of soybean oil to conjugated soybean oil under mild reaction conditions and in high yields. No hydrogenation products are detected with any of these catalysts. Preliminary physical tests have shown that the conjugated soybean oil has exceptional drying properties and the resulting coatings exhibit good solvent resistance. The [RhCl(C 8 H 14 ) 2 ] 2 catalyst provides similarly high yields of other conjugated vegetable oils, conjugated linoleic acid, and conjugated ethyl linoleate. Other rhodium catalysts, such as RhCl(PPh 3 ) 3 , have also been found to be effective for the conjugation of ethyl linoleate.

Soybean oil

10.1007/s11746-001-0284-1

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Citations (111)

A Convenient Procedure for the Preparation of Levoglucosenone and Its Conversion to Novel Chiral Derivatives

ChemInform (2004)

Walter S. Trahanovsky Jason M. Ochaoda Chen Wang Kevin D. Revell Kirk Arvidson

Abstract For Abstract see ChemInform Abstract in Full Text.

10.1002/chin.200411231

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Citations (4)

Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement

The Journal of Organic Chemistry (1997)

G. W. DAUB James P. Edwards Carol R. Okada Jana Westran Allen Claudia Tata Maxey

The ortho ester Claisen rearrangement of trisubstituted allylic alcohols exhibits significant levels of diastereoselection. In E allylic alcohols, a 1,3-diaxial interaction develops in the chairlike transition state leading to the anti isomer, rendering the reaction syn selective by a factor of 3-5 to 1. In Z allylic alcohols, the 1,3-diaxial interaction develops in the transition state leading to the syn isomer, generating an anti:syn selectivity of 6-15 to 1. The relative stereochemistry of the syn isomer was confirmed independently by the synthesis of the mycotoxin botryodiplodin.

10.1021/jo9614250

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Citations (39)

Protonation of rhenium 1,3-enyne and 1,3-diyne complexes: formation of exo-alkylidene η3-allyl and η3-propargyl complexes

Inorganica Chimica Acta (2002)

Charles P. Casey Steven Chung

Propargyl

Alkyne

Enyne

Alkene

10.1016/s0020-1693(02)00740-5

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