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Volumn 9, Issue 13, 2007, Pages 2605-2607

Reactions of dimethoxycarbene with dimethyl 2,3-dicycanomaleate and fumarate

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EID: 34547153159 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol071143u Document Type: Article

Times cited : (8)

References (12)

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2
- 34547183927
- A few minor impurities remain. Compound 6 was obtained as primary product by thermolysis of 1.3 equiv of the DMC source in benzene in the presence of fumarate 2 or maleate 3. in a degassed, sealed tube at 50 °C for 24 h. Nearly pure 6 was isolated from the reaction mixture by washing with hexane to remove most of the p-methoxyacetophenone byproduct. Any attempt to prepare a pure sample of 6 led to its hydrolysis and formation of succinates 7. The yield of the crude 6 exceeded 90, 1H NMR (600 MHz, CDCl3) δ 3.50 (s, 3H, 3.68 (s. 3H, 3.91 (s. 3H, 4.14 (s, 3H, 13C NMR (150.9 MHz, CDCl3) δ 52.8, 53.5, 54.7. 59.0, 59.5, 59.8, 112.6, 113.4, 120.6, 162.8, 168.1; HRMS (CI, NH3) m/z calcd for C11H13N2O6 M, H, 269.0774, found 269.0766
- + 269.0774, found 269.0766.

4
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- For example: a
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6
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- (c) Tidwell, T. T. Sri. Synth. 2006, 23, 391.
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7
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