Synthesis of 5,5-Dimethyl-4-Vinylidihydrofuran-2(3)-One and 6,6-Dimethyl-5-(2-Oxopropyl)Tetrahydro-2-PYRAN-2-One from (+)-3-Carene

Shavaleeva, G.A.; Ivanova, N. A.; Miftakhov, M.S.

doi:10.7868/S3034630425110159

PII

S3034630425110159-1

DOI

10.7868/S3034630425110159

Publication type

Status

Published

Authors

G.A. Shavaleeva

Affiliation: Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

N. A. Ivanova

Affiliation: Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

M.S. Miftakhov

Affiliation: Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Volume/ Edition

Volume 61 / Issue number 11

Pages

1644-1648

Abstract

5,5-Dimethyl-4-vinylidihydrofuran-2(3)-one and 6,6-dimethyl- 5-(2-oxopropyl)tetrahydro-2-pyran-2-one were synthesized by intramolecular cyclization of vicinal- disubstituted dimethylcyclopropane α,ω amide- and ketoesters obtained by oxidative cleavage of (+)- 3- carene with methanesulfonic acid.

Keywords

(+)-3-карен окислительная дециклизация реакция Шмидта вицинальный α,ω-амидоэфир внутримолекулярная циклизация 5,5-диметил-4R-винилдигидрофуран-2(3H)-он диметилциклопропан 6,6-диметил-5-(2-оксопропил)тетрагидро-2H-пиран-2-он

Date of publication

26.08.2025

Year of publication

2025

Number of purchasers

Views

References

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2. Nair L.G., Saksena A., Lovey R., Sannigrahi M., Wong J., Kong J., Fu X., Girĳavallabhan V. J. Org. Chem. 2010, 75 (4), 1285–1288. https://doi.org/10.1021/jo9022759
3. Liu J-J., Ni Z-B., Li L., Wei K., and Yang Y-R. J. Am. Chem. Soc. 2025, 147, 16792−16797. https://doi.org/10.1021/jaсs.5c05000
4. Gopichand Y., Khanra A.S., Mitra R.B., Chakravarti K.K. Indian J. Chem. 1975, 13, 433–436.
5. Kondo K., Mori F. Chem. Lett. 1974, 741−742. https://doi.org/10.1246/cl.1974.741

GOST	Ivanova N., Miftakhov M., Shavaleeva G. Synthesis of 5,5-Dimethyl-4-Vinylidihydrofuran-2(3)-One and 6,6-Dimethyl-5-(2-Oxopropyl)Tetrahydro-2-PYRAN-2-One from (+)-3-Carene // Russian Journal of Organic Chemistry. – 2025. – V. 61. – Issue number 11 C. 1644-1648 . URL: https://orgchemras.ru/s3034630425110159-1/?version_id=124864. DOI: 10.7868/S3034630425110159
MLA	Ivanova, N. A, Miftakhov, M.S, Shavaleeva, G.A "Synthesis of 5,5-Dimethyl-4-Vinylidihydrofuran-2(3)-One and 6,6-Dimethyl-5-(2-Oxopropyl)Tetrahydro-2-PYRAN-2-One from (+)-3-Carene." Russian Journal of Organic Chemistry. 61.11 (2025).:1644-1648. DOI: 10.7868/S3034630425110159
APA	Ivanova N., Miftakhov M., Shavaleeva G. (2025). Synthesis of 5,5-Dimethyl-4-Vinylidihydrofuran-2(3)-One and 6,6-Dimethyl-5-(2-Oxopropyl)Tetrahydro-2-PYRAN-2-One from (+)-3-Carene. Russian Journal of Organic Chemistry. vol. 61, no. 11, pp.1644-1648 DOI: 10.7868/S3034630425110159

RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

Synthesis of 5,5-Dimethyl-4-Vinylidihydrofuran-2(3)-One and 6,6-Dimethyl-5-(2-Oxopropyl)Tetrahydro-2-PYRAN-2-One from (+)-3-Carene

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RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

Synthesis of 5,5-Dimethyl-4-Vinylidihydrofuran-2(3)-One and 6,6-Dimethyl-5-(2-Oxopropyl)Tetrahydro-2-PYRAN-2-One from (+)-3-Carene

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