Synthesis of strained pyridine-containing cyclyne via reductive aromatization

Journal of Organic Chemistry

Volumn 75, Issue 10, 2010, Pages 3537-3540

  Miki, Koji ^a   Fujita, Michiyasu ^a   Inoue, Yuki ^a   Senda, Yoshinori ^a   Kowada, Toshiyuki ^a   Ohe, Kouichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTION; CYCLOTRIMER; DIHYDROANTHRACENE; MACROCYCLIC COMPOUNDS;

AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL); TIN; TITANIUM COMPOUNDS;

OLEFINS;

ALKADIENE; CARBOHYDRATE; PYRIDINE;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; GEL PERMEATION CHROMATOGRAPHY; SONOGASHIRA REACTION; SYNTHESIS;

ALKYNES; CRYSTALLOGRAPHY, X-RAY; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRIDINES;

EID: 77952480363     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1006202     Document Type: Article

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39. Macrocycle 8a (R = H, n = 0) was detected by LRMS as well as HRMS, but other spectral data could not be measured because of low solubility in any organic solvents after evaporation. The macrocyclic structure of 8c was determined by X-ray crystal structure analysis. See the Supporting Information.
40. The reductive aromatization of 5a, 6a, and 7a (n = 0) did not proceed to give the corresponding cyclynes at all.
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42. The reductive aromatization of 8b also gave the corresponding cyclyne, but the cyclyne gradually decomposed under the reaction conditions. See the Supporting Information.
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45. The time-dependent (TD) calculation of the model cyclyne shown in Figure 2 indicates that the UV-vis absorption spectrum of 11 is reasonable. The results of calculation are summarized in the Supporting Information.