Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane

Ian M. Helps; David Parker; James Chapman; George Ferguson

doi:10.1039/C39880001094

Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane

Ian M. Helps
, David Parker^*
, James Chapman
, George Ferguson

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

56 Citations (Scopus)

Abstract

A general synthetic method for the synthesis of 1,8-disubstituted derivatives of the 14-membered tetra-aza macrocycle, 'cyclam', involves selective ditosylation: in the Cu²⁺ complex of the 1,8-diacetic acid derivative, the copper is six-co-ordinate with elongated Cu-O interactions and this macrocycle undergoes lactamisation to form a paracyclophane-like tricyclic lactam which is resistant to acidic hydrolysis.

Original language	English
Pages (from-to)	1094-1095
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Transactions
Issue number	16
DOIs	https://doi.org/10.1039/C39880001094
Publication status	Published - Aug 1988

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Helps, I. M., Parker, D., Chapman, J., & Ferguson, G. (1988). Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane. Journal of the Chemical Society, Chemical Transactions, (16), 1094-1095. https://doi.org/10.1039/C39880001094

Helps, Ian M. ; Parker, David ; Chapman, James et al. / Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane. In: Journal of the Chemical Society, Chemical Transactions. 1988 ; No. 16. pp. 1094-1095.

@article{3ae9fc8ca20c493393e0283ebfec7dca,

title = "Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane",

abstract = "A general synthetic method for the synthesis of 1,8-disubstituted derivatives of the 14-membered tetra-aza macrocycle, 'cyclam', involves selective ditosylation: in the Cu2+ complex of the 1,8-diacetic acid derivative, the copper is six-co-ordinate with elongated Cu-O interactions and this macrocycle undergoes lactamisation to form a paracyclophane-like tricyclic lactam which is resistant to acidic hydrolysis.",

author = "Helps, \{Ian M.\} and David Parker and James Chapman and George Ferguson",

note = "Publisher Copyright: @ The Royal Society of Chemistry, 1988.",

year = "1988",

month = aug,

doi = "10.1039/C39880001094",

language = "English",

pages = "1094--1095",

journal = "Journal of the Chemical Society, Chemical Transactions",

issn = "0022-4936",

publisher = "Royal Society of Chemistry",

number = "16",

}

Helps, IM, Parker, D, Chapman, J & Ferguson, G 1988, 'Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane', Journal of the Chemical Society, Chemical Transactions, no. 16, pp. 1094-1095. https://doi.org/10.1039/C39880001094

Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane. / Helps, Ian M.; Parker, David; Chapman, James et al.
In: Journal of the Chemical Society, Chemical Transactions, No. 16, 08.1988, p. 1094-1095.

Research output: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane

AU - Helps, Ian M.

AU - Parker, David

AU - Chapman, James

AU - Ferguson, George

PY - 1988/8

Y1 - 1988/8

N2 - A general synthetic method for the synthesis of 1,8-disubstituted derivatives of the 14-membered tetra-aza macrocycle, 'cyclam', involves selective ditosylation: in the Cu2+ complex of the 1,8-diacetic acid derivative, the copper is six-co-ordinate with elongated Cu-O interactions and this macrocycle undergoes lactamisation to form a paracyclophane-like tricyclic lactam which is resistant to acidic hydrolysis.

AB - A general synthetic method for the synthesis of 1,8-disubstituted derivatives of the 14-membered tetra-aza macrocycle, 'cyclam', involves selective ditosylation: in the Cu2+ complex of the 1,8-diacetic acid derivative, the copper is six-co-ordinate with elongated Cu-O interactions and this macrocycle undergoes lactamisation to form a paracyclophane-like tricyclic lactam which is resistant to acidic hydrolysis.

UR - https://www.scopus.com/pages/publications/37049076562

U2 - 10.1039/C39880001094

DO - 10.1039/C39880001094

M3 - Journal article

AN - SCOPUS:37049076562

SN - 0022-4936

SP - 1094

EP - 1095

JO - Journal of the Chemical Society, Chemical Transactions

JF - Journal of the Chemical Society, Chemical Transactions

IS - 16

ER -

Helps IM, Parker D, Chapman J, Ferguson G. Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane. Journal of the Chemical Society, Chemical Transactions. 1988 Aug;(16):1094-1095. doi: 10.1039/C39880001094

Selective N,N-functionalisation of cyclam: Crystal structure of the Cu 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.2 5.8]tetradecane

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