Synthesis of an Ortho-Triazacyclophane: N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene

Andria M. Panagopoulos; Matthias Zeller; Daniel P. Becker

doi:10.1021/jo1017074

Synthesis of an Ortho-Triazacyclophane: N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene

Andria M. Panagopoulos, Matthias Zeller, Daniel P. Becker

Department of Chemistry and Biochemistry

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

Abstract

N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene has been synthesized via sequential palladium-catalyzed Buchwald-Hartwig N-arylation reactions affording the 9-membered triaza o-cyclophane in 35% overall yield. An X-ray crystal structure shows the new cyclophane to have a C(2)-symmetric saddle conformation, as compared to the crown conformation exhibited by the related carbocyclic cyclotriveratrylene (CTV).

Original language	American English
Journal	Chemistry: Faculty Publications and Other Works
Volume	75
Issue number	22
DOIs	https://doi.org/10.1021/jo1017074
State	Published - Oct 25 2010

Keywords

ortho-Triazacyclophane

Disciplines

Chemistry

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Synthesis of an Ortho-Triazacyclophane NNN-TrimethyltribenzFinal published version, 352 KBLicense: Unspecified

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title = "Synthesis of an Ortho-Triazacyclophane: N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene",

abstract = " N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene has been synthesized via sequential palladium-catalyzed Buchwald-Hartwig N-arylation reactions affording the 9-membered triaza o-cyclophane in 35\% overall yield. An X-ray crystal structure shows the new cyclophane to have a C(2)-symmetric saddle conformation, as compared to the crown conformation exhibited by the related carbocyclic cyclotriveratrylene (CTV).",

keywords = "ortho-Triazacyclophane",

author = "Panagopoulos, \{Andria M.\} and Matthias Zeller and Becker, \{Daniel P.\}",

year = "2010",

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doi = "10.1021/jo1017074",

language = "American English",

volume = "75",

journal = "Chemistry: Faculty Publications and Other Works",

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T1 - Synthesis of an Ortho-Triazacyclophane: N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene

AU - Panagopoulos, Andria M.

AU - Zeller, Matthias

AU - Becker, Daniel P.

PY - 2010/10/25

Y1 - 2010/10/25

N2 - N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene has been synthesized via sequential palladium-catalyzed Buchwald-Hartwig N-arylation reactions affording the 9-membered triaza o-cyclophane in 35% overall yield. An X-ray crystal structure shows the new cyclophane to have a C(2)-symmetric saddle conformation, as compared to the crown conformation exhibited by the related carbocyclic cyclotriveratrylene (CTV).

AB - N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene has been synthesized via sequential palladium-catalyzed Buchwald-Hartwig N-arylation reactions affording the 9-membered triaza o-cyclophane in 35% overall yield. An X-ray crystal structure shows the new cyclophane to have a C(2)-symmetric saddle conformation, as compared to the crown conformation exhibited by the related carbocyclic cyclotriveratrylene (CTV).

KW - ortho-Triazacyclophane

UR - https://ecommons.luc.edu/chemistry_facpubs/34

U2 - 10.1021/jo1017074

DO - 10.1021/jo1017074

M3 - Article

VL - 75

JO - Chemistry: Faculty Publications and Other Works

JF - Chemistry: Faculty Publications and Other Works

IS - 22

ER -

Synthesis of an Ortho-Triazacyclophane: N,N',N''-Trimethyltribenzo-1,4,7-triazacyclononatriene

Abstract

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