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

• Main Author: Dhillon, Ranjit S. (Author)
• Corporate Author: SpringerLink (Online service)
• Format: Electronic eBook
• Language: English
• Published: Berlin, Heidelberg : Springer Berlin Heidelberg, 2007.
• Subjects: Chemistry.; Organic chemistry.; Medicinal chemistry.; Biochemistry.; Organic Chemistry.; Medicinal Chemistry.; Biochemistry, general.

 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. 

 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.