Geometry and aromaticity in highly strained heterocyclic allenes:: Characterization of a 2,3-didehydro-2H-thiopyran

被引：18
|
作者：
Nikitina, AF [1 ]
Sheridan, RS [1 ]
机构：
[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 20期
关键词：
D O I：
10.1021/ol051733x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly strained cyclic allene 2,3-didehydro-2H-thiopyran was generated by irradiation of matrix-isolated 2-benzothienylchlorocarbene and characterized by IR and UV/vis spectroscopy, in situ trapping, and DFT modeling. Calculations indicate that the allenic moiety in this system, although less aromatic in character, is relatively more stable than in the corresponding oxa system. It is suggested that the thio ring system can more readily accommodate the allenic geometry.
引用
收藏
页码：4467 / 4470
页数：4
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