Hydroboration and Organic Synthesis: 9-Borabicyclo [3.3.1] nonane (9-BBN) / Edition 1

by Ranjit S. Dhillon

Overview

9-Borabicyclo [3.3.1]nonane, a commercially available reagent, is the most versatile hydroborating reagent to synthesize organoboranes (B-R-9-BBN). The reagent exhibits remarkable regio-, chemo-, and stereoselectivity during hydroboration reactions. The organoboranes can be converted to C-H, C-O, C-N, C-S, C-halogen, C-metal and above all C-C bonds. In addition, the suitable substituted / unsaturated R of B-R-9-BBN can be utilized to produce dienes, enynes, allenes etc. with defined stereochemistry. 9-BBN’s derivatives have been elegantly used for the asymmetric reduction of ketone moiety. Diels-Alder and Suzuki reactions have expanded the utility of 9-BBN for the synthesis of a variety of organic compounds required for industry. Consequently, this vast field in the form of a book will be helpful to synthetic organic chemists for easy access to literature, required for chemical transformations.

Product Details

ISBN-13:	9783540490753
Publisher:	Springer Berlin Heidelberg
Publication date:	06/28/2007
Edition description:	2007
Pages:	586
Product dimensions:	6.10(w) x 9.25(h) x 0.06(d)

Table of Contents

General Remarks.- Preparation and Properties.- Kinetic Studies.- Hydroboration.- Synthesis of Alcohols.- Synthesis of Aldehydes and Ketones.- Synthesis of Carboxylic Acids.- Synthesis of Esters.- Synthesis of Nitriles.- Synthesis of (E)-?,?-Unsaturated Amides.- Synthesis of Amines.- Synthesis of Halides.- Synthesis of Dialkylsulfides.- Synthesis of Thiophene Oligomers.- Synthesis of Cyclopropanes and Cyclobutanes.- Synthesis of Borinanes.- Synthesis and Transformations of Butterflyboranes: cis-Bicyclo[3.3.0]oct-1-yldialkylboranes.- Synthesis of—-Bromoboranes.- Synthesis of Borinates.- Synthesis and Transformation of Polymers.- Synthesis of Alkali Metal 9-Boratabicyclo[3.3.1] nonane (Li, K, and Na 9-BBNH).- Synthesis of B-R-9-BBN Not Available via Hydroboration.- Synthesis of Unsaturated Compounds.- Reduction.- Asymmetric Reduction.- Cleavage of Ethers.- trans-Metalation.- Separation of Isomers.- Diels-Alder Reaction.- Suzuki Reaction.- Miscellaneous Reactions.