Title: Divergent Elementoboration: 1,3‐Haloboration versus 1,1‐Carboboration of Propargyl Esters

Citation
Wilkins LC, Soltani Y, Lawson JR, et al. (2018). Divergent Elementoboration: 1,3‐Haloboration versus 1,1‐Carboboration of Propargyl Esters. Cardiff University. http://doi.org/10.17035/d.2020.0098717132


Access Rights: Data is provided under a Creative Commons Attribution (CC BY 4.0) licence
Access Method: Click to email a request for this data to opendata@cardiff.ac.uk

Dataset Details
Publisher: Cardiff University
Date (year) of data becoming publicly available: 2018
Coverage start date: 01/01/2014
Coverage end date: 01/04/2018
Data format: .pdf, .cif, .jpg
Software Required: Mercury or similar to view Xray structures
Estimated total storage size of dataset: Less than 100 megabytes
DOI: 10.17035/d.2020.0098717132

Description

This work showcases the 1,3‐haloboration reaction of alkynes in which boron and chlorine add to propargyl systems in a proposed sequential oxazoliumborate formation with subsequent ring‐opening and chloride migration. In addition, the functionalization of these propargyl esters with dimethyl groups in the propargylic position leads to stark differences in reactivity whereby a formal 1,1‐carboboration prevails to give the 2,2‐dichloro‐3,4‐dihydrodioxaborinine products as an intramolecular chelate. Density functional theory calculations are used to rationalize the distinct carboboration and haloboration pathways. Significantly, this method represents a metal‐free route to highly functionalized compounds in a single step to give structurally complex products.

Data includes experimental procedures, X-ray data and NMR spectra.

Research results based upon these data are published at http://doi.org/10.1002/chem.201801493



Keywords

Reaction Mechanisms, Structure elucidation

Research Areas

Related Projects

Last updated on 2020-27-01 at 11:51