Photochemical generation and trapping of 3-oxacyclohexyne,Organic & Biomolecular Chemistry

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Photochemical generation and trapping of 3-oxacyclohexyne
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-09-15 00:00:00 , DOI: 10.1039/c7ob01697b
Rui Fan _{1,

2,

3,

4} , Yuewei Wen _{1,

2,

3,

4} , Dasan M. Thamattoor _{1,

2,

3,

4}

Affiliation

The strained heterocyclic alkyne, 3-oxacyclohexyne, was generated photochemically for the first time using a cyclopropanated phenanthrene precursor, and trapped by cyclopentadienones as Diels–Alder adducts. The precursor initially produced the putative 3-oxacyclopentylidenecarbene that subsequently rearranged to the cycloalkyne. Computational studies indicate that the carbene favors a singlet state, and the barrier for its ring expansion by a 1,2-shift of the carbon proximal to oxygen is lower in energy than the corresponding shift of the distal carbon.

中文翻译：

3-氧杂环己炔的光化学生成和捕获

首次使用环丙烷化的菲前体，通过光化学方法生成了应变杂环杂环炔基3-氧杂环己炔，并以环戊二烯酮的形式作为Diels-Alder加合物捕获。该前体最初产生了推定的3-氧杂环戊叉碳烯，随后将其重排成环炔烃。计算研究表明，卡宾偏向单线态，并且通过与近端碳的相应位移相比，通过碳的1，2-位移使它的环膨胀的壁垒的能量较低。

更新日期：2017-09-22

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