Metal-mediated trandem [6 + 2],homo[6 + 2] cycloadditions of alkynes to cycloheptatriene. Generation of novel tetracycloundecadienes

Journal of the American Chemical Society

Volumn 118, Issue 41, 1996, Pages 9980-9981

  Chen, Weichun ^a   Chaffee, Karen ^a   Chung, Hyei Jha ^a   Sheridan, John B ^a  

^a University Heights   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029909053     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961436a     Document Type: Article

References (27)

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24. 1H 2D (COSY) NMR spectra and high-resolution MS) were obtained for all new compounds reported (see supporting information).
25. 3] (1, 1-2 mmol) or 2 (1-2 mmol)) and the appropriate alkyne (3-5 mmol) in n-hexane (100-200 mL) was irradiated with UV light from a 450 W Hanovia Hg vapor lamp through Pyrex at a distance of ca. 5 cm until all of 1 or 2 had been consumed (IR, 4-48 h). Removal of the solvent in vacuo and purification of the residue on a silica gel column or by TLC gave the products 4a-e as clear colorless oils or white solids. The reactions proceed in good yields when higher concentrations of substrates are used, however the more intense color of these solutions necessitates longer reaction times.
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