volume 24 issue 16 pages 3028-3032

Insertion of S2 into Donor–Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides

Anu Jacob
Philip Barkawitz
Peter G. Jones
Daniel B. Werz
Publication typeJournal Article
Publication date2022-04-20
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A facile and efficient route to dithiolanes starting from donor-acceptor cyclopropanes is reported. Potassium p-toluenethiosulfonate has been established as the reagent of choice for this formal insertion of the disulfide moiety. Using this methodology, dithiolanes have been synthesized in moderate to good yields with high functional group tolerance. Upon treatment with an excess of mCPBA, the corresponding dithiolanes delivered four-membered thietane dioxides, the formal (3+1)-cycloaddition product of D-A cyclopropanes, and sulfur dioxide.
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GOST Copy
Jacob A. et al. Insertion of S2 into Donor–Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides // Organic Letters. 2022. Vol. 24. No. 16. pp. 3028-3032.
GOST all authors (up to 50) Copy
Jacob A., Barkawitz P., Jones P. G., Werz D. B. Insertion of S2 into Donor–Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides // Organic Letters. 2022. Vol. 24. No. 16. pp. 3028-3032.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.2c00967
UR - https://doi.org/10.1021/acs.orglett.2c00967
TI - Insertion of S2 into Donor–Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides
T2 - Organic Letters
AU - Jacob, Anu
AU - Barkawitz, Philip
AU - Jones, Peter G.
AU - Werz, Daniel B.
PY - 2022
DA - 2022/04/20
PB - American Chemical Society (ACS)
SP - 3028-3032
IS - 16
VL - 24
PMID - 35442042
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Jacob,
author = {Anu Jacob and Philip Barkawitz and Peter G. Jones and Daniel B. Werz},
title = {Insertion of S2 into Donor–Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.orglett.2c00967},
number = {16},
pages = {3028--3032},
doi = {10.1021/acs.orglett.2c00967}
}
MLA
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MLA Copy
Jacob, Anu, et al. “Insertion of S2 into Donor–Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides.” Organic Letters, vol. 24, no. 16, Apr. 2022, pp. 3028-3032. https://doi.org/10.1021/acs.orglett.2c00967.