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Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes

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Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes. / Evans, Daniel M.; Hughes, David D.; Murphy, Patrick J. et al.
In: Organometalics, Vol. 40, No. 15, 09.08.2021, p. 2496-2503.

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

HarvardHarvard

Evans, DM, Hughes, DD, Murphy, PJ, Horton, PN, Coles, SJ, de Biani, FF, Corsini, M & Butler, IR 2021, 'Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes', Organometalics, vol. 40, no. 15, pp. 2496-2503. https://doi.org/10.1021/acs.organomet.1c00256

APA

Evans, D. M., Hughes, D. D., Murphy, P. J., Horton, P. N., Coles, S. J., de Biani, F. F., Corsini, M., & Butler, I. R. (2021). Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes. Organometalics, 40(15), 2496-2503. https://doi.org/10.1021/acs.organomet.1c00256

CBE

Evans DM, Hughes DD, Murphy PJ, Horton PN, Coles SJ, de Biani FF, Corsini M, Butler IR. 2021. Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes. Organometalics. 40(15):2496-2503. https://doi.org/10.1021/acs.organomet.1c00256

MLA

Evans, Daniel M. et al. "Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes". Organometalics. 2021, 40(15). 2496-2503. https://doi.org/10.1021/acs.organomet.1c00256

VancouverVancouver

Evans DM, Hughes DD, Murphy PJ, Horton PN, Coles SJ, de Biani FF et al. Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes. Organometalics. 2021 Aug 9;40(15):2496-2503. Epub 2021 Jul 23. doi: 10.1021/acs.organomet.1c00256

Author

Evans, Daniel M. ; Hughes, David D. ; Murphy, Patrick J. et al. / Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes. In: Organometalics. 2021 ; Vol. 40, No. 15. pp. 2496-2503.

RIS

TY - JOUR

T1 - Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes

AU - Evans, Daniel M.

AU - Hughes, David D.

AU - Murphy, Patrick J.

AU - Horton, Peter N.

AU - Coles, Simon J.

AU - de Biani, Fabrizia Fabrizi

AU - Corsini, Maddalena

AU - Butler, Ian R.

N1 - doi: 10.1021/acs.organomet.1c00256

PY - 2021/8/9

Y1 - 2021/8/9

N2 - An efficient synthesis of 1,1′,2,2′-tetraiodoferrocene is described that uses 1,1′,2,2′-tetrakis(tri-n-butylstannyl)ferrocene as a key intermediate in its synthesis. In an attempt to examine the stepwise mechanism, the reaction of the tetratin-substituted ferrocene 1,1′,2,2′-tetrakis(tri-n-butylstannyl)ferrocene with iodine was monitored by 1H NMR and a series of coexisting intermediate compounds such as 1,1′-bis(tri-n-butylstannyl)-2,2′-diodoferrocene were observed. The crystal structure of 1,1′,2,2′-tetraiodoferrocene has been determined, and it is compared with the structure of the previously reported 1,1′,2,2′-tetrabromoferrocene and 1,2,4,1′-tetraiodoferrocene. The comparative electrochemistry of 1,1′,2,2′-tetrachloroferrocene, 1,1′,2,2′-tetrabromoferrocene, and 1,1′,2,2′-tetraiodoferrocene is described. The crystal structure of 1,2,1′-triiodoferrocene is also reported for comparative use to illustrate the scope of the synthetic method.

AB - An efficient synthesis of 1,1′,2,2′-tetraiodoferrocene is described that uses 1,1′,2,2′-tetrakis(tri-n-butylstannyl)ferrocene as a key intermediate in its synthesis. In an attempt to examine the stepwise mechanism, the reaction of the tetratin-substituted ferrocene 1,1′,2,2′-tetrakis(tri-n-butylstannyl)ferrocene with iodine was monitored by 1H NMR and a series of coexisting intermediate compounds such as 1,1′-bis(tri-n-butylstannyl)-2,2′-diodoferrocene were observed. The crystal structure of 1,1′,2,2′-tetraiodoferrocene has been determined, and it is compared with the structure of the previously reported 1,1′,2,2′-tetrabromoferrocene and 1,2,4,1′-tetraiodoferrocene. The comparative electrochemistry of 1,1′,2,2′-tetrachloroferrocene, 1,1′,2,2′-tetrabromoferrocene, and 1,1′,2,2′-tetraiodoferrocene is described. The crystal structure of 1,2,1′-triiodoferrocene is also reported for comparative use to illustrate the scope of the synthetic method.

U2 - 10.1021/acs.organomet.1c00256

DO - 10.1021/acs.organomet.1c00256

M3 - Article

VL - 40

SP - 2496

EP - 2503

JO - Organometalics

JF - Organometalics

SN - 0276-7333

IS - 15

ER -