Anodic olefin coupling reactions involving ketene dithioacetals: Evidence for a 'radical-type' cyclization

Yongmao Sun; Kevin D. Moeller

doi:10.1016/S0040-4039(02)01663-5

Anodic olefin coupling reactions involving ketene dithioacetals: Evidence for a 'radical-type' cyclization

Yongmao Sun, Kevin D. Moeller

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

A series of anodic coupling reactions between ketene dithioacetal groups and enol ethers have been studied in order to probe why some of the cyclizations are successful while other closely related attempts fail. It has been found that the success of the cyclization reactions strongly depends on the location of substituents on the olefins. The reactions are highly sensitive to substituents on the terminating olefin but not to substituents on the initial radical cation. This behavior is consistent with what has been observed previously with radical cyclization reactions.

Original language	English
Pages (from-to)	7159-7161
Number of pages	3
Journal	Tetrahedron Letters
Volume	43
Issue number	40
DOIs	https://doi.org/10.1016/S0040-4039(02)01663-5
State	Published - Sep 30 2002

Access to Document

10.1016/S0040-4039(02)01663-5

Cite this

@article{b60bb2988db44643b9ceb0b4c543dfea,

title = "Anodic olefin coupling reactions involving ketene dithioacetals: Evidence for a 'radical-type' cyclization",

abstract = "A series of anodic coupling reactions between ketene dithioacetal groups and enol ethers have been studied in order to probe why some of the cyclizations are successful while other closely related attempts fail. It has been found that the success of the cyclization reactions strongly depends on the location of substituents on the olefins. The reactions are highly sensitive to substituents on the terminating olefin but not to substituents on the initial radical cation. This behavior is consistent with what has been observed previously with radical cyclization reactions.",

author = "Yongmao Sun and Moeller, {Kevin D.}",

note = "Funding Information: We thank the National Science Foundation (CHE-9023698) for their generous support of this work. We also gratefully acknowledge the Washington University High Resolution NMR facility, partially supported by NIH grants RR02004, RR05018, and RR07155, and the Washington University Mass Spectrometry Resource Center, partially supported by NIHRR00954, for their assistance.",

year = "2002",

month = sep,

day = "30",

doi = "10.1016/S0040-4039(02)01663-5",

language = "English",

volume = "43",

pages = "7159--7161",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "40",

}

TY - JOUR

T1 - Anodic olefin coupling reactions involving ketene dithioacetals

T2 - Evidence for a 'radical-type' cyclization

AU - Sun, Yongmao

AU - Moeller, Kevin D.

N1 - Funding Information: We thank the National Science Foundation (CHE-9023698) for their generous support of this work. We also gratefully acknowledge the Washington University High Resolution NMR facility, partially supported by NIH grants RR02004, RR05018, and RR07155, and the Washington University Mass Spectrometry Resource Center, partially supported by NIHRR00954, for their assistance.

PY - 2002/9/30

Y1 - 2002/9/30

N2 - A series of anodic coupling reactions between ketene dithioacetal groups and enol ethers have been studied in order to probe why some of the cyclizations are successful while other closely related attempts fail. It has been found that the success of the cyclization reactions strongly depends on the location of substituents on the olefins. The reactions are highly sensitive to substituents on the terminating olefin but not to substituents on the initial radical cation. This behavior is consistent with what has been observed previously with radical cyclization reactions.

AB - A series of anodic coupling reactions between ketene dithioacetal groups and enol ethers have been studied in order to probe why some of the cyclizations are successful while other closely related attempts fail. It has been found that the success of the cyclization reactions strongly depends on the location of substituents on the olefins. The reactions are highly sensitive to substituents on the terminating olefin but not to substituents on the initial radical cation. This behavior is consistent with what has been observed previously with radical cyclization reactions.

UR - http://www.scopus.com/inward/record.url?scp=0037201148&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(02)01663-5

DO - 10.1016/S0040-4039(02)01663-5

M3 - Article

AN - SCOPUS:0037201148

SN - 0040-4039

VL - 43

SP - 7159

EP - 7161

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

Anodic olefin coupling reactions involving ketene dithioacetals: Evidence for a 'radical-type' cyclization

Abstract

Access to Document

Other files and links

Fingerprint

Cite this