Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 12
1,980
Views
32
CrossRef citations to date
0
Altmetric
Original Articles

“Instant Methylide” Modification of the Corey–Chaykovsky Epoxide Synthesis

, , , , &
Pages 2135-2143 | Received 17 Oct 2002, Published online: 17 Aug 2006
 

Abstract

We report that Me3S(O)+I (1) and Me3S+I (2) form stable, dry mixtures with KOt-Bu and NaH, respectively, which remain stable upon prolonged storage (>1 year). The corresponding methylides (Me2SO=CH2 and Me2S=CH2) are generated upon addition of DMSO or DMSO/THF solutions of carbonyl compounds, cleanly affording epoxides via the Corey–Chaykovsky reaction in good yields and short reaction times (as short as 20 min when 1–2 mmol of various ketones and aldehydes were treated with a mixture of 1 and KOt-Bu at 50–60°C).

Acknowledgments

We are grateful for the generous financial support provided by: the Fordham University Clare Boothe Luce Scholars Program (support for ALD); Mr. Stephen Bepler and Mr. Jack Walton, Members of the Fordham College at Rose Hill Board of Visitors (support for MS); the Fordham University Collegiate Science and Technology Entry Program (CSTEP) (support for CTT and RG); Research Corporation Cottrell College Science Award No. C-3698; and the National Science Foundation's Division of Undergraduate Education through grant DUE #9650684.

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 422.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.