Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexes

C. Roe; E. J. Sandoe; G. R. Stephenson

doi:10.1016/j.tetlet.2009.11.052

Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexes

C. Roe, E. J. Sandoe, G. R. Stephenson

Chemistry of Materials and Catalysis

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

4 Citations (Scopus)

Abstract

Acid-catalysed solvolysis procedures exchange protecting groups on benzyl alcohol derivatives in the synthesis of eta(5) 1-arylcyclohexadienyliron building blocks for alkaloid synthesis. The reaction proceeds via a carbocation intermediate which can also be intercepted by intramolecular electrophilic addition to the tricarbonyl(eta(4)-diene)iron(0) moiety to provide a novel and high-yielding cyclisation reaction forming a 5a alpha-cyanomethyl-5a,8a-dihydrofluorene tricarbonyliron complex in 96% yield. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	591-595
Number of pages	5
Journal	Tetrahedron Letters
Volume	51
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2009.11.052
Publication status	Published - 2010

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10.1016/j.tetlet.2009.11.052

Cite this

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title = "Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexes",

abstract = "Acid-catalysed solvolysis procedures exchange protecting groups on benzyl alcohol derivatives in the synthesis of eta(5) 1-arylcyclohexadienyliron building blocks for alkaloid synthesis. The reaction proceeds via a carbocation intermediate which can also be intercepted by intramolecular electrophilic addition to the tricarbonyl(eta(4)-diene)iron(0) moiety to provide a novel and high-yielding cyclisation reaction forming a 5a alpha-cyanomethyl-5a,8a-dihydrofluorene tricarbonyliron complex in 96% yield. (C) 2009 Elsevier Ltd. All rights reserved.",

author = "C. Roe and Sandoe, {E. J.} and Stephenson, {G. R.}",

note = "Roe, Caroline Sandoe, Elizabeth J. Stephenson, G. Richard",

year = "2010",

doi = "10.1016/j.tetlet.2009.11.052",

language = "English",

volume = "51",

pages = "591--595",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "4",

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TY - JOUR

T1 - Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexes

AU - Roe, C.

AU - Sandoe, E. J.

AU - Stephenson, G. R.

N1 - Roe, Caroline Sandoe, Elizabeth J. Stephenson, G. Richard

PY - 2010

Y1 - 2010

N2 - Acid-catalysed solvolysis procedures exchange protecting groups on benzyl alcohol derivatives in the synthesis of eta(5) 1-arylcyclohexadienyliron building blocks for alkaloid synthesis. The reaction proceeds via a carbocation intermediate which can also be intercepted by intramolecular electrophilic addition to the tricarbonyl(eta(4)-diene)iron(0) moiety to provide a novel and high-yielding cyclisation reaction forming a 5a alpha-cyanomethyl-5a,8a-dihydrofluorene tricarbonyliron complex in 96% yield. (C) 2009 Elsevier Ltd. All rights reserved.

AB - Acid-catalysed solvolysis procedures exchange protecting groups on benzyl alcohol derivatives in the synthesis of eta(5) 1-arylcyclohexadienyliron building blocks for alkaloid synthesis. The reaction proceeds via a carbocation intermediate which can also be intercepted by intramolecular electrophilic addition to the tricarbonyl(eta(4)-diene)iron(0) moiety to provide a novel and high-yielding cyclisation reaction forming a 5a alpha-cyanomethyl-5a,8a-dihydrofluorene tricarbonyliron complex in 96% yield. (C) 2009 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2009.11.052

DO - 10.1016/j.tetlet.2009.11.052

M3 - Article

VL - 51

SP - 591

EP - 595

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 4

ER -