Organic Letters

, том 3 , издание 4 , страницы 581-584

Photorearrangement of Vinylidenecyclopropanes to 1,2,3-Butatriene Derivatives

Kazuhiko Mizuno ¹

Hajime Maeda ¹

Hikaru Sugita ¹

Shogo Nishioka ¹

Takayoshi Hirai ¹

Akira Sugimoto ¹

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Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai, Osaka 599-8531, Japan |

Тип публикации: Journal Article

Дата публикации: 2001-01-30

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

БС1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/ol000379u

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PubMed ID: 11178830

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

Photoirradiation of benzene solutions containing 1-diarylvinylidene-2,2,3,3-tetramethylcyclopropanes (2a−d) afforded rearranged products 1,2,3-butatrienes (3a−d) in good to high yields. Photorearrangement from 2,2,3-trimethyl and 2,2- and 2,3-dimethyl derivatives 2e−g also proceeded, but the rates of the rearrangement were lower than those of 2a−d. A singlet mechanism is proposed for this photorearrangement, where alkyl migration occurs from 1,3-biradical intermediates generated via the homolysis of the C1−C2 bond. Generation of diarylvinylidene carbenes from 1,3-biradicals might be competitive with the formation of 3.

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Московский государственный университет имени М.В. Ломоносова

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Mizuno K. et al. Photorearrangement of Vinylidenecyclopropanes to 1,2,3-Butatriene Derivatives // Organic Letters. 2001. Vol. 3. No. 4. pp. 581-584.

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Mizuno K., Maeda H., Sugita H., Nishioka S., Hirai T., Sugimoto A. Photorearrangement of Vinylidenecyclopropanes to 1,2,3-Butatriene Derivatives // Organic Letters. 2001. Vol. 3. No. 4. pp. 581-584.

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TY - JOUR

DO - 10.1021/ol000379u

UR - https://doi.org/10.1021/ol000379u

TI - Photorearrangement of Vinylidenecyclopropanes to 1,2,3-Butatriene Derivatives

T2 - Organic Letters

AU - Mizuno, Kazuhiko

AU - Maeda, Hajime

AU - Sugita, Hikaru

AU - Nishioka, Shogo

AU - Hirai, Takayoshi

AU - Sugimoto, Akira

PY - 2001

DA - 2001/01/30

PB - American Chemical Society (ACS)

SP - 581-584

IS - 4

VL - 3

PMID - 11178830

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2001_Mizuno,

author = {Kazuhiko Mizuno and Hajime Maeda and Hikaru Sugita and Shogo Nishioka and Takayoshi Hirai and Akira Sugimoto},

title = {Photorearrangement of Vinylidenecyclopropanes to 1,2,3-Butatriene Derivatives},

journal = {Organic Letters},

year = {2001},

volume = {3},

publisher = {American Chemical Society (ACS)},

month = {jan},

url = {https://doi.org/10.1021/ol000379u},

number = {4},

pages = {581--584},

doi = {10.1021/ol000379u}

}

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Mizuno, Kazuhiko, et al. “Photorearrangement of Vinylidenecyclopropanes to 1,2,3-Butatriene Derivatives.” Organic Letters, vol. 3, no. 4, Jan. 2001, pp. 581-584. https://doi.org/10.1021/ol000379u.

Издатель

American Chemical Society (ACS)

Журнал

Organic Letters

scimago Q1

wos Q1

БС1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)