Reactions of α-lithio (aminocarbene)tungsten anions with diiodoalkanes

Synthesis of (μ-bis(aminocarbene))ditungsten complexes

David W. Macomber, Puttannachetty Madhukar

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Treatment of (CO)5W[C(N(CH3)2)CH3] (1) with nBuLi followed by 5-10 equiv. of a diiodoalkane (diiodomethane, 1,2-diiodoethane, 1,3-diiodopropane, 1,4-diiodobutane, or 1,5-diiodopentane) gave the respective (iodoalkylaminocarbene)tungsten complexes (CO)5W[C(N(CH3)2)CH2(CH2)nI] (n=1-5) (2). For the reaction of the α-lithio anion of 1 with diiodomethane, only a 5% yield of the corresponding complex 2a (n = 1) was obtained. Moreover, the reaction of the α-lithio anion of 1 with 1,2-diiodoethane gave no product 2b (n = 2). On the other hand, good to excellent yields (69-93%) of complexes 2c-e (n = 3-5) were obtained using 1,3-diiodopropane, 1,4-diiodobutane, or 1,5-diiodopentane. Complexes 2c-e were further treated with the α-lithio anion of 1 to afford the new (μ-bis(aminocarbene))ditungsten complexes (CO)5W[C(N(CH3) 2)CH2(CH2)nCH2C(N(CH3)2)]W(CO)5 (n=3-5) (3c-e) in yields ranging from 52 to 61%.

Original languageEnglish (US)
Pages (from-to)279-285
Number of pages7
JournalJournal of Organometallic Chemistry
Volume433
Issue number3
DOIs
StatePublished - Jul 28 1992

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Tungsten
Anions
tungsten
Negative ions
anions
synthesis
products
methylene iodide
aminocarbene
1,4-diiodobutane

Cite this

Reactions of α-lithio (aminocarbene)tungsten anions with diiodoalkanes : Synthesis of (μ-bis(aminocarbene))ditungsten complexes. / Macomber, David W.; Madhukar, Puttannachetty.

In: Journal of Organometallic Chemistry, Vol. 433, No. 3, 28.07.1992, p. 279-285.

Research output: Contribution to journalArticle

@article{28351dde23d2462fa3041348b5828a05,
title = "Reactions of α-lithio (aminocarbene)tungsten anions with diiodoalkanes: Synthesis of (μ-bis(aminocarbene))ditungsten complexes",
abstract = "Treatment of (CO)5W[C(N(CH3)2)CH3] (1) with nBuLi followed by 5-10 equiv. of a diiodoalkane (diiodomethane, 1,2-diiodoethane, 1,3-diiodopropane, 1,4-diiodobutane, or 1,5-diiodopentane) gave the respective (iodoalkylaminocarbene)tungsten complexes (CO)5W[C(N(CH3)2)CH2(CH2)nI] (n=1-5) (2). For the reaction of the α-lithio anion of 1 with diiodomethane, only a 5{\%} yield of the corresponding complex 2a (n = 1) was obtained. Moreover, the reaction of the α-lithio anion of 1 with 1,2-diiodoethane gave no product 2b (n = 2). On the other hand, good to excellent yields (69-93{\%}) of complexes 2c-e (n = 3-5) were obtained using 1,3-diiodopropane, 1,4-diiodobutane, or 1,5-diiodopentane. Complexes 2c-e were further treated with the α-lithio anion of 1 to afford the new (μ-bis(aminocarbene))ditungsten complexes (CO)5W[C(N(CH3) 2)CH2(CH2)nCH2C(N(CH3)2)]W(CO)5 (n=3-5) (3c-e) in yields ranging from 52 to 61{\%}.",
author = "Macomber, {David W.} and Puttannachetty Madhukar",
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T1 - Reactions of α-lithio (aminocarbene)tungsten anions with diiodoalkanes

T2 - Synthesis of (μ-bis(aminocarbene))ditungsten complexes

AU - Macomber, David W.

AU - Madhukar, Puttannachetty

PY - 1992/7/28

Y1 - 1992/7/28

N2 - Treatment of (CO)5W[C(N(CH3)2)CH3] (1) with nBuLi followed by 5-10 equiv. of a diiodoalkane (diiodomethane, 1,2-diiodoethane, 1,3-diiodopropane, 1,4-diiodobutane, or 1,5-diiodopentane) gave the respective (iodoalkylaminocarbene)tungsten complexes (CO)5W[C(N(CH3)2)CH2(CH2)nI] (n=1-5) (2). For the reaction of the α-lithio anion of 1 with diiodomethane, only a 5% yield of the corresponding complex 2a (n = 1) was obtained. Moreover, the reaction of the α-lithio anion of 1 with 1,2-diiodoethane gave no product 2b (n = 2). On the other hand, good to excellent yields (69-93%) of complexes 2c-e (n = 3-5) were obtained using 1,3-diiodopropane, 1,4-diiodobutane, or 1,5-diiodopentane. Complexes 2c-e were further treated with the α-lithio anion of 1 to afford the new (μ-bis(aminocarbene))ditungsten complexes (CO)5W[C(N(CH3) 2)CH2(CH2)nCH2C(N(CH3)2)]W(CO)5 (n=3-5) (3c-e) in yields ranging from 52 to 61%.

AB - Treatment of (CO)5W[C(N(CH3)2)CH3] (1) with nBuLi followed by 5-10 equiv. of a diiodoalkane (diiodomethane, 1,2-diiodoethane, 1,3-diiodopropane, 1,4-diiodobutane, or 1,5-diiodopentane) gave the respective (iodoalkylaminocarbene)tungsten complexes (CO)5W[C(N(CH3)2)CH2(CH2)nI] (n=1-5) (2). For the reaction of the α-lithio anion of 1 with diiodomethane, only a 5% yield of the corresponding complex 2a (n = 1) was obtained. Moreover, the reaction of the α-lithio anion of 1 with 1,2-diiodoethane gave no product 2b (n = 2). On the other hand, good to excellent yields (69-93%) of complexes 2c-e (n = 3-5) were obtained using 1,3-diiodopropane, 1,4-diiodobutane, or 1,5-diiodopentane. Complexes 2c-e were further treated with the α-lithio anion of 1 to afford the new (μ-bis(aminocarbene))ditungsten complexes (CO)5W[C(N(CH3) 2)CH2(CH2)nCH2C(N(CH3)2)]W(CO)5 (n=3-5) (3c-e) in yields ranging from 52 to 61%.

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