Reactions of alkenyl Fischer carbene complexes with ketene acetals: Formation of alkynes

Siu Ling B. Wang; Xuejun Liu; Miriam C. Ruiz; Vijay Gopalsamuthiram; William D. Wulff

doi:10.1002/ejoc.200600672

Reactions of alkenyl Fischer carbene complexes with ketene acetals: Formation of alkynes

Siu Ling B. Wang, Xuejun Liu, Miriam C. Ruiz, Vijay Gopalsamuthiram, William D. Wulff

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

10 Scopus citations

Abstract

Alkenyl Fischer carbene complexes with an isopropoxy group on the carbene carbon will react with ketene acetals by 1,4-addition to give a zwitterionic intermediate, which undergoes subsequent internal isopropoxide transfer to generate a vinylidene complex. Either a hydrogen or phenyl group on the vinylidene carbon will undergo a formal 1,2-migration to give 4-pentynoate esters after hydrolysis of the intermediate orthoester.

Original language	English (US)
Pages (from-to)	5219-5224
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	23
DOIs	https://doi.org/10.1002/ejoc.200600672
State	Published - Nov 27 2006
Externally published	Yes

Keywords

Fischer carbene complex
Ketene acetal
Michael addition
Rearrangement
Vinylidene complex

Access

10.1002/ejoc.200600672

OpenUrl availability

Full text

Cite this

@article{10e4516ce500438ebfc503eef3932b0b,

title = "Reactions of alkenyl Fischer carbene complexes with ketene acetals: Formation of alkynes",

abstract = "Alkenyl Fischer carbene complexes with an isopropoxy group on the carbene carbon will react with ketene acetals by 1,4-addition to give a zwitterionic intermediate, which undergoes subsequent internal isopropoxide transfer to generate a vinylidene complex. Either a hydrogen or phenyl group on the vinylidene carbon will undergo a formal 1,2-migration to give 4-pentynoate esters after hydrolysis of the intermediate orthoester.",

keywords = "Fischer carbene complex, Ketene acetal, Michael addition, Rearrangement, Vinylidene complex",

author = "Wang, {Siu Ling B.} and Xuejun Liu and Ruiz, {Miriam C.} and Vijay Gopalsamuthiram and Wulff, {William D.}",

year = "2006",

month = nov,

day = "27",

doi = "10.1002/ejoc.200600672",

language = "English (US)",

pages = "5219--5224",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "23",

}

TY - JOUR

T1 - Reactions of alkenyl Fischer carbene complexes with ketene acetals

T2 - Formation of alkynes

AU - Wang, Siu Ling B.

AU - Liu, Xuejun

AU - Ruiz, Miriam C.

AU - Gopalsamuthiram, Vijay

AU - Wulff, William D.

PY - 2006/11/27

Y1 - 2006/11/27

N2 - Alkenyl Fischer carbene complexes with an isopropoxy group on the carbene carbon will react with ketene acetals by 1,4-addition to give a zwitterionic intermediate, which undergoes subsequent internal isopropoxide transfer to generate a vinylidene complex. Either a hydrogen or phenyl group on the vinylidene carbon will undergo a formal 1,2-migration to give 4-pentynoate esters after hydrolysis of the intermediate orthoester.

AB - Alkenyl Fischer carbene complexes with an isopropoxy group on the carbene carbon will react with ketene acetals by 1,4-addition to give a zwitterionic intermediate, which undergoes subsequent internal isopropoxide transfer to generate a vinylidene complex. Either a hydrogen or phenyl group on the vinylidene carbon will undergo a formal 1,2-migration to give 4-pentynoate esters after hydrolysis of the intermediate orthoester.

KW - Fischer carbene complex

KW - Ketene acetal

KW - Michael addition

KW - Rearrangement

KW - Vinylidene complex

UR - http://www.scopus.com/inward/record.url?scp=33845468974&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33845468974&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200600672

DO - 10.1002/ejoc.200600672

M3 - Article

AN - SCOPUS:33845468974

SN - 1434-193X

SP - 5219

EP - 5224

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 23

ER -

Reactions of alkenyl Fischer carbene complexes with ketene acetals: Formation of alkynes

Abstract

Keywords

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this