N-Protected Amines During Hydroboration/OXIDATION Synthesis of N-Alkyl Diaikylphosphoramidopropanal

Baboulène, M.; Lattes, Armand; Benmaarouf‐Khallaayoun, Z.

doi:10.1080/00397919008053143

Cited by 10 publications

(1 citation statement)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There has been a growing interest in surfactants over the last two decades not only from a fundamental point of view but also for applications in chemical synthesis and elsewhere. − These amphiphilic molecules decrease interactions at interfaces via their surface active properties, and they are classified as ionic, zwitterionic, or nonionic . In the course of studies on the hydroboration of unsaturated amines, − we envisaged a new family of surfactants with hydrophilic heads containing a boron atom. A polar head derived from the affinity of boron for nitrogen appeared to be feasible, which would then be linked to a long-chain alkyl moiety to form an amphiphilic compound.…”

Section: Introductionmentioning

confidence: 99%

First Example of Surfactants Enclosing a Semipolar Nitrogen−Boron Bond

and

Baboulène

1996

Langmuir

View full text Add to dashboard Cite

We describe a new surfactant family whose hydrophilic head contains a semipolar N+−B- bond in a stable aminopropylborane structure. These compounds were synthesized by hydroboration of allylic amines with good yields (>90%). Parameters characterizing their surface activity (critical micelle concentration, surface tension, superficial excess, molecular area at the water−air interface) along with the phase diagram in a water−isooctane−butanol system were determined. The compounds show promise for use in organized molecular systems (OMS).

show abstract

Section: Introductionmentioning

confidence: 99%

First Example of Surfactants Enclosing a Semipolar Nitrogen−Boron Bond

and

Baboulène

1996

Langmuir

View full text Add to dashboard Cite

show abstract

Hydroboration

Zaidlewicz

2000

Kirk-Othmer Encyclopedia of Chemical Technology

View full text Add to dashboard Cite

The hydroboration reaction and transformations of its organoborane products are described. The mechanism and the chemo‐, regio‐, and stereoselectivity of the hydroboration reaction are presented, as well as the synthesis and characteristics of the most common hydroborating agents. Transformations of organoboranes may involve carbon‐hetero atom bond formation and lead to stereoselective synthesis of organic halides, amines, aziridines, sulfur, selenium, and mercury compounds. Hydroboration‐protonolysis is a nonocatalytic method of cis‐hydrogenation of multiple bonds. Hydroboration‐oxidation is a standard method for cis‐anti‐Markovnikov hydroxylation of multiple bonds. Carbon‐carbon bond formation can be accomplished by transformation of organoboranes through coupling of groups attached to boron, cross‐coupling of organoboranes with organic halides, organoborate rearrangements providing access to alkynes, ( E )‐ and ( Z )‐alkenes, ( E,E )‐, ( E,Z )‐, ( Z,Z )‐dienes, and enynes. Single‐carbon insertion reactions include carbonylation, cyanidation, and the DCME and related reactions. Other reactions include α‐ and β‐alkylation of carbonyl compounds, the addition of alkynyl, alkenyl, and allylic boranes to aldehydes, leading to proparylic alcohols and stereodefined allylic and homoallylic alcohols, boron‐stabilized carbanions, the boron Wittig reaction, and concerted reactions of allylic and vinylic boranes. Contrathermodynamic isomerization of olefins is discussed. The synthesis of boron‐containing polymers and of isotopically labeled compounds is covered. Asymmetric synthesis via chiral organoboranes is covered in detail.

show abstract