Interaction of aryloxychlorocarbenes with acetylenedicarboxylate: Novel formation of polyfunctional butadienes and 8-oxatricyclo[3.2.1.0 2.4]oct-6-enes

Ying Cheng; Qing Zhu; Quan Song Li; Otto Meth-Cohn

doi:10.1021/jo0501792

Interaction of aryloxychlorocarbenes with acetylenedicarboxylate: Novel formation of polyfunctional butadienes and 8-oxatricyclo[3.2.1.0 ^2.4]oct-6-enes

Ying Cheng^*
, Qing Zhu
, Quan Song Li
, Otto Meth-Cohn

^*Corresponding author for this work

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

13 Citations (Scopus)

Abstract

The interaction of aryloxychlorocarbenes with dialkyl acetylenedicarboxylates has been examined. Thermolyses of 3-aryloxy-3- chlorodiazirines in the presence of acetylenedicarboxylate resulted in the formation of unexpected polyfunctional 1,3-butadienes and 8-oxatricyclo[3.2.1. 0^2.4]oct-6-enes or of 2-aryoxycarbonylmaleates dependent upon reaction conditions. This work confirmed the nucleophilicity of aryloxychlorocarbenes and underlined their synthetic potential.

Original language	English
Pages (from-to)	4840-4846
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	70
Issue number	12
DOIs	https://doi.org/10.1021/jo0501792
Publication status	Published - 12 Jun 2005
Externally published	Yes

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title = "Interaction of aryloxychlorocarbenes with acetylenedicarboxylate: Novel formation of polyfunctional butadienes and 8-oxatricyclo[3.2.1.0 2.4]oct-6-enes",

abstract = "The interaction of aryloxychlorocarbenes with dialkyl acetylenedicarboxylates has been examined. Thermolyses of 3-aryloxy-3- chlorodiazirines in the presence of acetylenedicarboxylate resulted in the formation of unexpected polyfunctional 1,3-butadienes and 8-oxatricyclo[3.2.1. 02.4]oct-6-enes or of 2-aryoxycarbonylmaleates dependent upon reaction conditions. This work confirmed the nucleophilicity of aryloxychlorocarbenes and underlined their synthetic potential.",

author = "Ying Cheng and Qing Zhu and Li, \{Quan Song\} and Otto Meth-Cohn",

year = "2005",

month = jun,

day = "12",

doi = "10.1021/jo0501792",

language = "English",

volume = "70",

pages = "4840--4846",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Interaction of aryloxychlorocarbenes with acetylenedicarboxylate

T2 - Novel formation of polyfunctional butadienes and 8-oxatricyclo[3.2.1.0 2.4]oct-6-enes

AU - Cheng, Ying

AU - Zhu, Qing

AU - Li, Quan Song

AU - Meth-Cohn, Otto

PY - 2005/6/12

Y1 - 2005/6/12

N2 - The interaction of aryloxychlorocarbenes with dialkyl acetylenedicarboxylates has been examined. Thermolyses of 3-aryloxy-3- chlorodiazirines in the presence of acetylenedicarboxylate resulted in the formation of unexpected polyfunctional 1,3-butadienes and 8-oxatricyclo[3.2.1. 02.4]oct-6-enes or of 2-aryoxycarbonylmaleates dependent upon reaction conditions. This work confirmed the nucleophilicity of aryloxychlorocarbenes and underlined their synthetic potential.

AB - The interaction of aryloxychlorocarbenes with dialkyl acetylenedicarboxylates has been examined. Thermolyses of 3-aryloxy-3- chlorodiazirines in the presence of acetylenedicarboxylate resulted in the formation of unexpected polyfunctional 1,3-butadienes and 8-oxatricyclo[3.2.1. 02.4]oct-6-enes or of 2-aryoxycarbonylmaleates dependent upon reaction conditions. This work confirmed the nucleophilicity of aryloxychlorocarbenes and underlined their synthetic potential.

UR - https://www.scopus.com/pages/publications/20344374157

U2 - 10.1021/jo0501792

DO - 10.1021/jo0501792

M3 - Article

AN - SCOPUS:20344374157

SN - 0022-3263

VL - 70

SP - 4840

EP - 4846

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

Interaction of aryloxychlorocarbenes with acetylenedicarboxylate: Novel formation of polyfunctional butadienes and 8-oxatricyclo[3.2.1.0 ^2.4]oct-6-enes

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