eprintid: 22309
rev_number: 22
userid: 1418
dir: disk0/00/02/23/09
datestamp: 2014-07-18 20:58:29
lastmod: 2021-06-23 14:55:05
status_changed: 2014-07-18 20:58:29
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Curran, DP
creators_name: Hadida, S
creators_name: Kim, SY
creators_name: Luo, Z
creators_email: curran@pitt.edu
creators_email: 
creators_email: 
creators_email: 
creators_id: CURRAN
creators_id: 
creators_id: 
creators_id: 
title: Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: Eight members of a new family of highly fluorinated (fluorous) tin hydrides have been synthesized and studied as reagents for radical reactions. Tin hydrides of the general formulas [Rf(CH2)(n)]3SnH-and [Rf(CH2)(n)]Me2SnH have been prepared where Rf is C4F9, C6F13, C8F17, or C10F21 and n is 2 or 3. These reagents are highly soluble in fluorinated solvents, and partition coefficients between perfluorohexanes and several organic solvents have been measured. The reagents are generally useful for reductive radical reactions and hydrostannation reactions that would typically be conducted with tributyltin hydride. Stoichiometric and catalytic procedures have been developed, and both feature very easy separation of the tin products from the organic products by convenient liquid-liquid or solid-liquid extractions. The tin reagents are recovered from reactions in high yields and are routinely reused. Rate constant measurements suggest that the fluorous tin hydrides are about as reactive as (or in some cases, slightly more reactive than) tributyltin hydride. The reagents show excellent potential for large-scale application in 'green' (environmentally friendly) processes. In addition, they are useful for combinatorial and parallel synthesis applications both as reagents and as scavengers in phase-switching procedures.
date: 1999-07-21
date_type: published
publication: Journal of the American Chemical Society
volume: 121
number: 28
pagerange: 6607 - 6615
refereed: TRUE
issn: 0002-7863
id_number: 10.1021/ja990069a
citation:   Curran, DP and Hadida, S and Kim, SY and Luo, Z  (1999) Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions.  Journal of the American Chemical Society, 121 (28).  6607 - 6615.  ISSN 0002-7863     
document_url: http://d-scholarship-dev.library.pitt.edu/22309/1/licence.txt