Aldrich Chemical Company, Inc.

Aldrich-boranes, Inc.

The Dow Chemical Company

Sigma-aldrich Co. LLC

Other

Exxon Research and Engineering Company

Purdue Research Foundation

Herbert C Brown

Christian T Goralski

Bakthan Singaram

Walter Weissman

George M Kramer

Rowland Pettit, Deceased

Borane-trialkylamine hydroboration agents

New, economical and convenient procedures for the preparation of catecholborane in high chemically pure form using tri-O-phenylene bis borate readily prepared from the reaction of catechol with boric acid, and diborane or borane-Lewis base complexes.

Economical and convenient procedures for the synthesis of catecholborane

Highly reactive hydroborating agents dioxane-monochloroborane and dioxane-dichloroborane are provided. Also provided by this invention are methods for producing dioxane-monochloroborane, dioxane-dichloroborane and methods for hydroborating olefins with these reagents.

Dioxane-monochloroborane and dioxane-dichloroborane

A borane-sulfide represented by the formula

Borane-sulfide hydroboration agents

A novel class of enolboration reagents represented by the formula

Dicyclooctylhaloboranes

Borane-N,N-dialkylanilines represented by the formula

Borane-N,N-dialkylaniline hydroboration agents

Novel borane adducts of hydroxydialkylsulfide borate esters represented by formula ##STR1## wherein R is straight or branched chain alkyl or alkoxy having from 2 to 5 carbon atoms and n is 1 to 3 inclusive. The compound are new hydroboration agents.

Borane-hydroxydialkylsulfide borates

Borane-N,N-diisopropylalkylamines as represented by the formula:

Borane-N,N-diisopropylalkylamine hydroboration agents

Bis(bicyclo(2.2.2)octyl)haloboranes

A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group. attached to boron, B is boron and Me is methyl.

Method of producing primary amines in high yields

A process for preparing a dimethylorganoborane represented by the formula R*BMe.sub.2 wherein R* is a chiral organyl group attached to the boron, B is boron and Me is methyl comprising treating a chiral boronic ester R*B(OR').sub.2 with a methyl magnesium salt or trimethylaluminum wherein R* is the same chiral organyl group and R' is alkyl.

Process for producing dimethylorganoboranes

A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo and a process for preparing.

Process of synthesizing chemically and optically pure

A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group,attached to boron, B is boron and Me is methyl.

Method of producing primary amines in high yields and novel

A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.

Optically active dimethylorganoboranes

A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.

Growing community of inventors

West Lafayette, IN, United States of America

Herbert C Brown