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Volumn 14, Issue 47, 1973, Pages 4711-4714

Ketene thioacetal monoxides: A novel and versatile class of two-carbon michael receptors

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343416210 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)87317-2 Document Type: Article

Times cited : (60)

References (9)

1
- 84918755604
- J.L. Herrmann, J.E. Richman, P.J. Wepplo, and R.H. Schlessinger, Tetrahedron Letts., in press.

2
- 84918725837
- Ketene thioacetals are reported to add alkyl and aryl organolithium reagents but reactions of these systems with other types of anions are unknown. For examples, see
- (1969) Angew. Chem. Intern. Ed. Engl. , vol.12 , pp. 1973
- Seebach¹ Kolb² Grobel³

3
- 33746365678
- Synthesis of 4-hydroxy-2-cyclopenten-1-ones via 1,3-dithianes
- This construction of a 1,4-dicarbonyl system is much more efficient than that obtained by alkylation with the acetal of chloroacetaldehyde. For a high yield example of that latter reaction, see
- (1972) Tetrahedron Letters , pp. 3735
- Woessner¹ Ellison²

4
- 84918753297
- Acylation of the carbonyl anion equivalent described in reference 1 with formaldehyde also gives a good yield of I. However, we have found that anhydrous formaldehyde is not convenient to handle on a large scale.

5
- 84918755033
- An alternative and comparable method of preparing II is described in reference 1.

6
- 84918709254
- Hydrolysis of these adducts to the intermediate keto thioacetal monoxide is done in refluxing water.

7
- 84918743505
- These reactions require between 5 and 15 hours at room temperature.

8
- 84918745997
- These reactions are worked up using saturated ammonium chloride. The yields reported are for isolated products. All compounds exhibited satisfactory spectral and physical properties.

9
- 84918755530
- For more detailed hydrolysis conditions, see reference 1 and references cited therein.

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