Synthesis of polynuclear aromatic compounds through net [5+5]-cycloaddition of 2-alkynylarylcarbene complexes and enyne-aldehyde derivatives

Tetrahedron Letters

Volumn 47, Issue 30, 2006, Pages 5303-5306

  Zhang, Yanshi ^a   Herndon, James W ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

Alkynes; Carbene complexes; Diels Alder reaction; Polynuclear aromatics; Pyrones

Indexed keywords

ALDEHYDE DERIVATIVE; CARBENOID; PHENANTHRENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33745212670     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.127     Document Type: Article

References (22)

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11. These complexes were prepared from 1,2-dibromobenzene or 2-iodo-1-bromobenzene in a sequence involving Sonogashira coupling, followed by lithiation of the resulting 1-alknynyl-2-bromobenzene derivative and conversion to the carbene complex. For a detailed procedure, see Ref. 2.
12. The compounds were prepared from 2,3-dibromothiophene (or 2,3-dibromofuran) in a sequence involving selective lithiation at the 2-position and formylation using DMF, followed by Sonogashira coupling using the resulting 3-bromo-2-thiophenecarboxaldehyde derivative (or furan analog). For a detailed procedure, see Ref. 6.
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15. The calculations were done at the MM2 level. This is a relatively low level of theory, however, this method provides the most direct measure for the parameter angle strain.
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