Note
2-(Diethylamino)ethanethiol, a New Reagent for the Odorless Deprotection of Aromatic Methyl Ethers
Purchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract

A new reagent for the deprotection of aromatic methyl ethers, 2-(diethylamino)ethanethiol, is reported. This compound, commercially available as its HCl salt, affords the corresponding phenols in good to excellent yields on a wide variety of substrates. A clear advantage of this method over the use of more common thiols, such as ethanethiol, is the easy extraction of both the deprotecting reagent and the byproduct 2-(diethylamino)ethyl methyl sulfide into the aqueous phase by quenching with dilute acid, which allows an essentially odorless workup.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 4 ACS Journal articles (4 most recent appear below).

Unexpected Binding Orientation of Bulky-B-Ring Anti-Androgens and Implications for Future Drug Targets
Charles B. Duke, III, Amanda Jones, Casey E. Bohl, James T. Dalton, and Duane D. MillerJournal of Medicinal Chemistry2011 Article ASAPUnexpected Binding Orientation of Bulky-B-Ring Anti-Androgens and Implications for Future Drug Targets
Charles B. Duke, III, Amanda Jones, Casey E. Bohl, James T. Dalton, and Duane D. MillerJournal of Medicinal Chemistry2011 Article ASAPSeveral new androgen receptor antagonists were synthesized and found to have varying activities across typically anti-androgen resistant mutants (Thr877 → Ala and Trp741 → Leu) and markedly improved potency over previously reported pan-antagonists. X-ray ...

Oxidation of Organotrifluoroborates via Oxone
Gary A. Molander and Livia N. CavalcantiThe Journal of Organic Chemistry2011 76 (2), 623-630Oxidation of Organotrifluoroborates via Oxone
Gary A. Molander and Livia N. CavalcantiThe Journal of Organic Chemistry2011 76 (2), 623-630A method for the oxidation of organotrifluoroborates using Oxone was developed. A variety of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates were converted into the corresponding oxidized products in excellent yields. This method proved to be ...

Reconciling Icetexane Biosynthetic Connections with Their Chemical Synthesis: Total Synthesis of (±)-5,6-Dihydro-6α-hydroxysalviasperanol, (±)-Brussonol, and (±)-Abrotanone
Eric M. Simmons, Jennifer R. Yen, and Richmond SarpongOrganic Letters2007 9 (14), 2705-2708Reconciling Icetexane Biosynthetic Connections with Their Chemical Synthesis: Total Synthesis of (±)-5,6-Dihydro-6α-hydroxysalviasperanol, (±)-Brussonol, and (±)-Abrotanone
Eric M. Simmons, Jennifer R. Yen, and Richmond SarpongOrganic Letters2007 9 (14), 2705-2708A unified strategy for the chemical synthesis of the icetexane diterpenoids brussonol and 5,6-dihydro-6α-hydroxysalviasperanol has led to a structural revision of the recently isolated natural products abrotandiol and abrotanone.

Planar-to-Axial Chirality Relay in Phospharuthenocenes. A Rotationally Hindered 2-(2‘-Diphenylphosphinonaphth-1‘-yl)phospharuthenocene
Duncan Carmichael, Louis Ricard, and Nicolas SeebothOrganometallics2007 26 (12), 2964-2970Planar-to-Axial Chirality Relay in Phospharuthenocenes. A Rotationally Hindered 2-(2‘-Diphenylphosphinonaphth-1‘-yl)phospharuthenocene
Duncan Carmichael, Louis Ricard, and Nicolas SeebothOrganometallics2007 26 (12), 2964-2970Competing steric pressures within the coordination sphere of 2-(2‘-X-naphth-1‘-yl)-3,4-dimethyl-5-phenyl-η5-phospholyl(pentamethylcyclopentadienyl)ruthenium(II) complexes (X = OMe (1), OH (3), OTf (4), PPh2(O) (5), PPh2 (6)) give rise to a well-defined ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue September 01, 2006
- Received May 30, 2006
Cart

ACS
Network






