1,6-C-H insertion of alkylidenecarbenes in 1-naphthol and 1-anthrol derivatives

Ken S. Feldman; Angela L. Perkins

doi:10.1016/S0040-4039(01)01208-4

1,6-C-H insertion of alkylidenecarbenes in 1-naphthol and 1-anthrol derivatives

Ken S. Feldman, Angela L. Perkins

Chemistry (Twin Cities)

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

44 Scopus citations

Abstract

Rare 1,6-C-H insertion of naphthol- and anthrol-derived alkylidenecarbenes has been observed in modest yield. Reaction in deuterated solvent did not provide any evidence in support of a reaction mechanism that requires exchange of the migrating proton with solvent. The pyran-annelated aromatic products are formed only when opportunities for the more common 1,5-C-H insertion process are blocked.

Original language	English (US)
Pages (from-to)	6031-6033
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(01)01208-4
State	Published - Aug 27 2001

Bibliographical note

Funding Information:
We thank the National Institutes of Health (GM37681) for financial support of this work.

Keywords

Alkylidenecarbene
Alkynyliodonium
C-H insertion
Peri position

Access

10.1016/S0040-4039(01)01208-4

OpenUrl availability

Full text

Cite this

@article{7762e798ab274d919d34b536ae3d0602,

title = "1,6-C-H insertion of alkylidenecarbenes in 1-naphthol and 1-anthrol derivatives",

abstract = "Rare 1,6-C-H insertion of naphthol- and anthrol-derived alkylidenecarbenes has been observed in modest yield. Reaction in deuterated solvent did not provide any evidence in support of a reaction mechanism that requires exchange of the migrating proton with solvent. The pyran-annelated aromatic products are formed only when opportunities for the more common 1,5-C-H insertion process are blocked.",

keywords = "Alkylidenecarbene, Alkynyliodonium, C-H insertion, Peri position",

author = "Feldman, {Ken S.} and Perkins, {Angela L.}",

note = "Funding Information: We thank the National Institutes of Health (GM37681) for financial support of this work.",

year = "2001",

month = aug,

day = "27",

doi = "10.1016/S0040-4039(01)01208-4",

language = "English (US)",

volume = "42",

pages = "6031--6033",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "35",

}

TY - JOUR

T1 - 1,6-C-H insertion of alkylidenecarbenes in 1-naphthol and 1-anthrol derivatives

AU - Feldman, Ken S.

AU - Perkins, Angela L.

N1 - Funding Information: We thank the National Institutes of Health (GM37681) for financial support of this work.

PY - 2001/8/27

Y1 - 2001/8/27

N2 - Rare 1,6-C-H insertion of naphthol- and anthrol-derived alkylidenecarbenes has been observed in modest yield. Reaction in deuterated solvent did not provide any evidence in support of a reaction mechanism that requires exchange of the migrating proton with solvent. The pyran-annelated aromatic products are formed only when opportunities for the more common 1,5-C-H insertion process are blocked.

AB - Rare 1,6-C-H insertion of naphthol- and anthrol-derived alkylidenecarbenes has been observed in modest yield. Reaction in deuterated solvent did not provide any evidence in support of a reaction mechanism that requires exchange of the migrating proton with solvent. The pyran-annelated aromatic products are formed only when opportunities for the more common 1,5-C-H insertion process are blocked.

KW - Alkylidenecarbene

KW - Alkynyliodonium

KW - C-H insertion

KW - Peri position

UR - http://www.scopus.com/inward/record.url?scp=0035959487&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035959487&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)01208-4

DO - 10.1016/S0040-4039(01)01208-4

M3 - Article

AN - SCOPUS:0035959487

SN - 0040-4039

VL - 42

SP - 6031

EP - 6033

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

1,6-C-H insertion of alkylidenecarbenes in 1-naphthol and 1-anthrol derivatives

Abstract

Bibliographical note

Keywords

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this