Acetyl Cation Facilitated Cyclizations of Olefinic Aldehydes. III.¹ Factors Determining Regiochemistry in Acroleins

Niels H. Andersen Department of Chemistry, University of Washington, Seattle, WA, 98195

David W. Ladner Department of Chemistry, University of Washington, Seattle, WA, 98195

Ana L. Moore Department of Chemistry, University of Washington, Seattle, WA, 98195

Abstract

Recent reports^3,4 of the use of Ac₂O-HClO₄-EtOAc as a reagent for the cyclizations of olefinic carbonyl compounds in other laboratories

contrast with our experience with the formation of six-membered rings by this procedure, and prompt us to report an unsuccessful approach to the cadalene sesquiterpenes which failed due to a preference for the 1,2- rather than 1,4-addition regiochemistry. Further results for non-conjugated aldehydes (ref. 3 and present study) provide a mechanistic rationale for the regiospecificities observed.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Acetyl Cation Facilitated Cyclizations of Olefinic Aldehydes. III.¹ Factors Determining Regiochemistry in Acroleins

Information for

Open access

Opportunities

Help and information

Acetyl Cation Facilitated Cyclizations of Olefinic Aldehydes. III.1 Factors Determining Regiochemistry in Acroleins

Abstract

Reprints and Corporate Permissions

Academic Permissions

Related research

To cite this article:

Download citation

Information for

Open access

Opportunities

Help and information

Keep up to date

Your download is now in progress and you may close this window

Login or register to access this feature

Acetyl Cation Facilitated Cyclizations of Olefinic Aldehydes. III.¹ Factors Determining Regiochemistry in Acroleins