Synthesis of 2-iodoynamides and regioselective [2+2] cycloadditions with ketene

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2111-2114

  Wang, Yu Pu ^a   Danheiser, Rick L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

2+2 cycloadditions; Cyclobutenones; Ketene; Ynamides

Indexed keywords

2 IODOYNAMIDE; IODINE DERIVATIVE; KETENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLOADDITION;

EID: 79953182290     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.002     Document Type: Article

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59. Reaction at higher concentration led to precipitation of the cyclobutenone product and clogging at the outlet of the needle in the reaction mixture.
60. 2O. Ketene was bubbled into the pale yellow reaction mixture with vigorous stirring at rt over a period of 4 h. The resulting brown solution was then concentrated to afford 0.308 g of a brown solid. Column chromatography on 20 g of silica gel (gradient elution with 15-55% EtOAc-hexanes) afforded 0.200 g of an off-white solid. Recrystallization from 3 mL of CH3CN at -20 °C furnished 0.181 g (86%) of cyclobutenone 15 as colorless needles.
61. Strong J-coupling was observed between the alkene carbon bearing the nitrogen substituent and the C-4 methylene protons. Strong coupling was also observed between the C-1 carbonyl carbon and these protons. Only weak coupling of the alkene carbon bearing iodine to the methylene protons was noted.
62. 3, 357.9935; found 357.9922.
63. 3) at 1-h intervals to determine the concentration of ynamide and cyclobutenone versus the internal standard.