Acid-Catalyzed Rearrangement of [5.n.2]Propella-e-lactones

Kiyomi Kakiuchi; Toshinori Tsugaru; Tobe Yoshito; Yoshinobu Odaira

doi:10.1021/jo00334a020

Acid-Catalyzed Rearrangement of [5.n.2]Propella-e-lactones

Kiyomi Kakiuchi^*, Toshinori Tsugaru, Tobe Yoshito, Yoshinobu Odaira

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

The acid-catalyzed rearrangement of [5.3.2]- and [5.4.2]propella-e-lactones 9 and 10 in boiling acetic acid takes place readily to afford the 1,2-disubstituted cyclopentene 21 and cyclohexene 26 as the major products, respectively, while such lactone ring cleavage of the [4.3.2]- and [4.4.2]propella-δ-lactones 1 and 2 does not occur at all under similar conditions. The remarkable distinction in reactivity in the acid-catalyzed rearrangement between the e-lactones and the δ-lactones is attributed to the effect of lactone ring size.

Original language	English
Pages (from-to)	4204-4208
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	46
Issue number	21
DOIs	https://doi.org/10.1021/jo00334a020
State	Published - 1 Jan 1981

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title = "Acid-Catalyzed Rearrangement of [5.n.2]Propella-e-lactones",

abstract = "The acid-catalyzed rearrangement of [5.3.2]- and [5.4.2]propella-e-lactones 9 and 10 in boiling acetic acid takes place readily to afford the 1,2-disubstituted cyclopentene 21 and cyclohexene 26 as the major products, respectively, while such lactone ring cleavage of the [4.3.2]- and [4.4.2]propella-δ-lactones 1 and 2 does not occur at all under similar conditions. The remarkable distinction in reactivity in the acid-catalyzed rearrangement between the e-lactones and the δ-lactones is attributed to the effect of lactone ring size.",

author = "Kiyomi Kakiuchi and Toshinori Tsugaru and Tobe Yoshito and Yoshinobu Odaira",

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T1 - Acid-Catalyzed Rearrangement of [5.n.2]Propella-e-lactones

AU - Kakiuchi, Kiyomi

AU - Tsugaru, Toshinori

AU - Yoshito, Tobe

AU - Odaira, Yoshinobu

PY - 1981/1/1

Y1 - 1981/1/1

N2 - The acid-catalyzed rearrangement of [5.3.2]- and [5.4.2]propella-e-lactones 9 and 10 in boiling acetic acid takes place readily to afford the 1,2-disubstituted cyclopentene 21 and cyclohexene 26 as the major products, respectively, while such lactone ring cleavage of the [4.3.2]- and [4.4.2]propella-δ-lactones 1 and 2 does not occur at all under similar conditions. The remarkable distinction in reactivity in the acid-catalyzed rearrangement between the e-lactones and the δ-lactones is attributed to the effect of lactone ring size.

AB - The acid-catalyzed rearrangement of [5.3.2]- and [5.4.2]propella-e-lactones 9 and 10 in boiling acetic acid takes place readily to afford the 1,2-disubstituted cyclopentene 21 and cyclohexene 26 as the major products, respectively, while such lactone ring cleavage of the [4.3.2]- and [4.4.2]propella-δ-lactones 1 and 2 does not occur at all under similar conditions. The remarkable distinction in reactivity in the acid-catalyzed rearrangement between the e-lactones and the δ-lactones is attributed to the effect of lactone ring size.

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EP - 4208

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 21

ER -

Acid-Catalyzed Rearrangement of [5.n.2]Propella-e-lactones

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