/ E-Alerts

Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides

Malcolm J. D’Souza and Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132. https://doi.org/10.3762/bjoc.18.13

Cite the Following Article

Malcolm J. D’Souza and Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132. https://doi.org/10.3762/bjoc.18.13

How to Cite

D’Souza, M. J.; Kevill, D. N. Beilstein J. Org. Chem. 2022, 18, 120–132. doi:10.3762/bjoc.18.13

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

File format:

RIS

BibTeX

Include:

Citation for the article above

Citation and complete reference list for the article above

Download

TY  - JOUR
A1  - D’Souza, Malcolm J.
A1  - Kevill, Dennis N.
T1  - Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 120
EP  - 132
SN  - 1860-5397
DO  - 10.3762/bjoc.18.13
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.13
KW  - correlation
KW  - Grunwald–Winstein equation
KW  - Hammett equation
KW  - mechanism
KW  - solvolysis
KW  - sulfonyl halides
N2  - There have been several studies on the solvolysis mechanisms for alkanesulfonyl chlorides (RSO2Cl) and arenesulfonyl chlorides (ArSO2Cl). The earlier of these studies were reviewed a little over thirty years ago by Gordon, Maskill and Ruasse (Chem. Soc. Rev. 1989, 18, 123–151) in a contribution entitled “Sulfonyl Transfer Reactions”. The present review will emphasize more recent contributions and, in particular, the application of the extended Grunwald–Winstein equation and kinetic solvent isotope effects to the solvolysis reactions. There is also an appreciable number of reports concerning the corresponding anhydrides with the chloride leaving group replaced by the appropriate sulfonate leaving group, concerning sulfamoyl chlorides (ZZ'NSO2Cl) with Z and Z' being alkyl or aryl and concerning the solvolysis of chlorosulfate esters (alkoxy- or aryloxysulfonyl chlorides), with the structures ROSO2Cl or ArOSO2Cl. The solvolyses of these additional types of sulfur(VI) substrates will be the topics of a future review.
ER  -

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG	Size: 6.6 MB	Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

Lan, R.; Yager, B.; Jee, Y.; Day, C. S.; Jones, A. C. Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination. Beilstein journal of organic chemistry 2024, 20, 479–496. doi:10.3762/bjoc.20.43
Liashuk, O. S.; Andriashvili, V. A.; Tolmachev, A. O.; Grygorenko, O. O. Chemoselective Reactions of Functionalized Sulfonyl Halides. Chemical record (New York, N.Y.) 2023, 24, e202300256. doi:10.1002/tcr.202300256

Explore citations to this article at

Back To Article

Other Beilstein-Institut Open Science Activities

aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)