Metal catalysed rearrangement of cyclopropanespiro-β-lactones to 2-furanones

Niall W.A. Geraghty; Paul A. Murphy

doi:10.1016/S0040-4039(00)73482-4

Metal catalysed rearrangement of cyclopropanespiro-β-lactones to 2-furanones

Niall W.A. Geraghty
, Paul A. Murphy

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

10 Citations (Scopus)

Abstract

The rearrangement of 5-oxo-4-oxaspiro[2.3]hexanes (cyclopropanespiro-β-lactones) to 2(5H)-furanones and 2(3H)-furanones is shown to be a general reaction which is promoted by metal catalysts. A mechanism is proposed, involving the novel insertion of a metal species into the OC_β bond of the β-lactone ring, which explains the basic features of the reaction, including its regioselectivity.

Original language	English
Pages (from-to)	6737-6740
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4039(00)73482-4
Publication status	Published - 5 Sept 1994

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title = "Metal catalysed rearrangement of cyclopropanespiro-β-lactones to 2-furanones",

abstract = "The rearrangement of 5-oxo-4-oxaspiro[2.3]hexanes (cyclopropanespiro-β-lactones) to 2(5H)-furanones and 2(3H)-furanones is shown to be a general reaction which is promoted by metal catalysts. A mechanism is proposed, involving the novel insertion of a metal species into the OCβ bond of the β-lactone ring, which explains the basic features of the reaction, including its regioselectivity.",

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AU - Geraghty, Niall W.A.

AU - Murphy, Paul A.

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Y1 - 1994/9/5

N2 - The rearrangement of 5-oxo-4-oxaspiro[2.3]hexanes (cyclopropanespiro-β-lactones) to 2(5H)-furanones and 2(3H)-furanones is shown to be a general reaction which is promoted by metal catalysts. A mechanism is proposed, involving the novel insertion of a metal species into the OCβ bond of the β-lactone ring, which explains the basic features of the reaction, including its regioselectivity.

AB - The rearrangement of 5-oxo-4-oxaspiro[2.3]hexanes (cyclopropanespiro-β-lactones) to 2(5H)-furanones and 2(3H)-furanones is shown to be a general reaction which is promoted by metal catalysts. A mechanism is proposed, involving the novel insertion of a metal species into the OCβ bond of the β-lactone ring, which explains the basic features of the reaction, including its regioselectivity.

UR - https://www.scopus.com/pages/publications/0028040796

U2 - 10.1016/S0040-4039(00)73482-4

DO - 10.1016/S0040-4039(00)73482-4

M3 - Article

AN - SCOPUS:0028040796

SN - 0040-4039

VL - 35

SP - 6737

EP - 6740

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Metal catalysed rearrangement of cyclopropanespiro-β-lactones to 2-furanones

Abstract

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