Wulff-Dotz Reaction

23 March, 2016 / by SK / in Reactions

5051

Overall Score4

Generality
Reagent Availability
Experimental User Friendliness
Criteria #4
Criteria #5

General Characteristics

The synthesis of phenols by reacting [alkoxy(vinyl)carbene]pentacarbonylchromium complexes (Fischer carbene complex) with alkenes is called the Wulff-Dotz reaction.

The immediate product of benzannulation is still complexed with the chromium atom. Oxidative treatment of the intermediate (e.g. O₂, CAN) gives the phenol product.

General References

Dotz, K. H. Angew. Chem. Int. Ed. 1975, 14, 644. DOI: 10.1002/anie.197506442
Dotz, K. H. Pure Appl. Chem. 1983, 55, 1689. doi:10.1351/pac198355111689
Dotz, K. H. New J. Chem. 1990, 14, 433.
Chamberlin, S.; Wulff, W. D. J. Org. Chem. 1994, 59: 3047. doi:10.1021/jo00090a024.
Waters, M. L.; Wulff, W. D. Org. React. 2008, 70, 121. doi: 10.1002/0471264180.or070.02

Reaction Mechanism

Ref: J. Am. Chem. Soc. 1981, 103, 7677.

Examples

The application to the synthesis of Fredericamycin A.^[1]

References

[1] (a) Boger, D. L.; Hueter, O.; Mbiya, K.; Zahang, M. J. Am. Chem. Soc. 1995, 117, 11839. doi:10.1021/ja00153a004 (b) Bpger. D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. doi:10.1021/jo00006a029