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The reactions of cyclotriphosphazene with 2-(2-hydroxyethylamino)ethanol. Spectroscopic studies of the derived products

The reactions of cyclotriphosphazene with 2-(2-hydroxyethylamino)ethanol. Spectroscopic studies of the derived products
The reactions of cyclotriphosphazene with 2-(2-hydroxyethylamino)ethanol. Spectroscopic studies of the derived products

The reactions of cyclotriphosphazene (1) with 2-(2-hydroxyethylamino)-ethanol (2) were investigated. 2-(2-hydroxyethylamino)-ethanol (2) is a tri-functional reagent consisting of both aliphatic hydroxyl and the secondary amino groups and its nucleophilic substitution reactions with cylotriphosphazene can lead to different product types; open chain, spiro, ansa, bridged and their mixtures. The reactions with one, two and three equimolar ratios of 2-(2-hydroxyethylamino)-ethanol, in the presence of NaH at 0–10 °C and at room temperature gave the following cyclotriphosphazene derivatives: one mono-spiro, N3P3Cl4[O–(CH2)2–NH–(CH2)2–O] (3, 1:1, r.t.); its isomer mono-ansa (5, 1:1, r.t.); one dispiro, N3P3Cl2[O–(CH2)2–NH–(CH2)2–O]2 (4, 1:1, r.t.); its isomer spiro-ansa (6, 1:2, r.t.); and one single-bridged compound with spiro substituted units, N3P3Cl3[O–(CH2)2–NH–(CH2)2–O]3N3P3Cl3 (7, 1:3, at 0–10 °C); as well as single-, N3P3Cl5[O–(CH2)2–NH–(CH2)2–O]N3P3Cl5 (8, 1:2, r.t.), double-, N3P3Cl4[O–(CH2)2–NH–(CH2)2–O]2N3P3Cl4 (9, 1:2, r.t.), and tri-bridged, N3P3Cl3[O–(CH2)2–NH–(CH2)2–O]3N3P3Cl3 (10, 1:3, at 0–10 °C) derivatives. Triple-bridged derivative is the major product in this system. The structures of the novel-derived compounds were characterized by TLC-MS, FT-IR, elemental analysis, 1H, and 31P NMR spectral.

2-(2-hydroxyethylamino)ethanol, ansa compound, bridged derivatives, Cylotriphosphazene, spiro compounds
1042-6507
454-463
Lee, Seung Seo
ee34fa26-5fb6-48c8-80c2-1f13ec4ccceb
Mizar, Pushpak
631b688c-b7fb-41d7-8038-9fb48ef935c7
Kucuk, Ozge
6484743b-51dd-438e-a4e6-f254b38ae7ee
Ture, Sedat
f8df6ec2-31e2-4212-b047-85bd660da1b4
Lee, Seung Seo
ee34fa26-5fb6-48c8-80c2-1f13ec4ccceb
Mizar, Pushpak
631b688c-b7fb-41d7-8038-9fb48ef935c7
Kucuk, Ozge
6484743b-51dd-438e-a4e6-f254b38ae7ee
Ture, Sedat
f8df6ec2-31e2-4212-b047-85bd660da1b4

Lee, Seung Seo, Mizar, Pushpak, Kucuk, Ozge and Ture, Sedat (2020) The reactions of cyclotriphosphazene with 2-(2-hydroxyethylamino)ethanol. Spectroscopic studies of the derived products. Phosphorus, Sulfur and Silicon and the Related Elements, 195 (6), 454-463. (doi:10.1080/10426507.2020.1712396).

Record type: Article

Abstract

The reactions of cyclotriphosphazene (1) with 2-(2-hydroxyethylamino)-ethanol (2) were investigated. 2-(2-hydroxyethylamino)-ethanol (2) is a tri-functional reagent consisting of both aliphatic hydroxyl and the secondary amino groups and its nucleophilic substitution reactions with cylotriphosphazene can lead to different product types; open chain, spiro, ansa, bridged and their mixtures. The reactions with one, two and three equimolar ratios of 2-(2-hydroxyethylamino)-ethanol, in the presence of NaH at 0–10 °C and at room temperature gave the following cyclotriphosphazene derivatives: one mono-spiro, N3P3Cl4[O–(CH2)2–NH–(CH2)2–O] (3, 1:1, r.t.); its isomer mono-ansa (5, 1:1, r.t.); one dispiro, N3P3Cl2[O–(CH2)2–NH–(CH2)2–O]2 (4, 1:1, r.t.); its isomer spiro-ansa (6, 1:2, r.t.); and one single-bridged compound with spiro substituted units, N3P3Cl3[O–(CH2)2–NH–(CH2)2–O]3N3P3Cl3 (7, 1:3, at 0–10 °C); as well as single-, N3P3Cl5[O–(CH2)2–NH–(CH2)2–O]N3P3Cl5 (8, 1:2, r.t.), double-, N3P3Cl4[O–(CH2)2–NH–(CH2)2–O]2N3P3Cl4 (9, 1:2, r.t.), and tri-bridged, N3P3Cl3[O–(CH2)2–NH–(CH2)2–O]3N3P3Cl3 (10, 1:3, at 0–10 °C) derivatives. Triple-bridged derivative is the major product in this system. The structures of the novel-derived compounds were characterized by TLC-MS, FT-IR, elemental analysis, 1H, and 31P NMR spectral.

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Accepted/In Press date: 3 January 2020
e-pub ahead of print date: 11 January 2020
Keywords: 2-(2-hydroxyethylamino)ethanol, ansa compound, bridged derivatives, Cylotriphosphazene, spiro compounds

Identifiers

Local EPrints ID: 438212
URI: http://eprints.soton.ac.uk/id/eprint/438212
ISSN: 1042-6507
PURE UUID: c5044bd5-1dda-45e4-add5-cd36fb3962db
ORCID for Seung Seo Lee: ORCID iD orcid.org/0000-0002-8598-3303

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Date deposited: 04 Mar 2020 17:31
Last modified: 26 Nov 2021 05:04

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Contributors

Author: Seung Seo Lee ORCID iD
Author: Pushpak Mizar
Author: Ozge Kucuk
Author: Sedat Ture

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