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C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media

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C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media. / Candeias, Nuno R.; Gois, Pedro M. P.; Veiros, Luis F.; Afonso, Carlos A. M.

In: Journal of Organic Chemistry, Vol. 73, No. 15, 01.08.2008, p. 5926-5932.

Research output: Contribution to journalArticleScientificpeer-review

Harvard

Candeias, NR, Gois, PMP, Veiros, LF & Afonso, CAM 2008, 'C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media', Journal of Organic Chemistry, vol. 73, no. 15, pp. 5926-5932. https://doi.org/10.1021/jo800980c

APA

Candeias, N. R., Gois, P. M. P., Veiros, L. F., & Afonso, C. A. M. (2008). C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media. Journal of Organic Chemistry, 73(15), 5926-5932. https://doi.org/10.1021/jo800980c

Vancouver

Candeias NR, Gois PMP, Veiros LF, Afonso CAM. C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media. Journal of Organic Chemistry. 2008 Aug 1;73(15):5926-5932. https://doi.org/10.1021/jo800980c

Author

Candeias, Nuno R. ; Gois, Pedro M. P. ; Veiros, Luis F. ; Afonso, Carlos A. M. / C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media. In: Journal of Organic Chemistry. 2008 ; Vol. 73, No. 15. pp. 5926-5932.

Bibtex - Download

@article{45e3f9a6e571442b88fd1e70d0bc877d,
title = "C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media",
abstract = "Light from a mercury vapor high-pressure lamp was used to induce the photolytic decomposition of alpha-diazo acetamides in hexane and in nonconventional media such as water or a film. The corresponding beta- and/or gamma-lactams were obtained in reasonable yields and in some cases with good diastereoselectivities with no need to use a metallic catalyst. Experimental studies on chiral substrates demonstrated the occurrence of insertion with retention of configuration.",
keywords = "CARBON-HYDROGEN INSERTION, ORGANIC-REACTIONS, AQUEOUS-MEDIA, WOLFF REARRANGEMENT, DIAZOCARBONYL COMPOUNDS, WATER, DECOMPOSITION, ESTERS, DIAZOACETAMIDES, STEREOCHEMISTRY",
author = "Candeias, {Nuno R.} and Gois, {Pedro M. P.} and Veiros, {Luis F.} and Afonso, {Carlos A. M.}",
year = "2008",
month = "8",
day = "1",
doi = "10.1021/jo800980c",
language = "English",
volume = "73",
pages = "5926--5932",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "AMER CHEMICAL SOC",
number = "15",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media

AU - Candeias, Nuno R.

AU - Gois, Pedro M. P.

AU - Veiros, Luis F.

AU - Afonso, Carlos A. M.

PY - 2008/8/1

Y1 - 2008/8/1

N2 - Light from a mercury vapor high-pressure lamp was used to induce the photolytic decomposition of alpha-diazo acetamides in hexane and in nonconventional media such as water or a film. The corresponding beta- and/or gamma-lactams were obtained in reasonable yields and in some cases with good diastereoselectivities with no need to use a metallic catalyst. Experimental studies on chiral substrates demonstrated the occurrence of insertion with retention of configuration.

AB - Light from a mercury vapor high-pressure lamp was used to induce the photolytic decomposition of alpha-diazo acetamides in hexane and in nonconventional media such as water or a film. The corresponding beta- and/or gamma-lactams were obtained in reasonable yields and in some cases with good diastereoselectivities with no need to use a metallic catalyst. Experimental studies on chiral substrates demonstrated the occurrence of insertion with retention of configuration.

KW - CARBON-HYDROGEN INSERTION

KW - ORGANIC-REACTIONS

KW - AQUEOUS-MEDIA

KW - WOLFF REARRANGEMENT

KW - DIAZOCARBONYL COMPOUNDS

KW - WATER

KW - DECOMPOSITION

KW - ESTERS

KW - DIAZOACETAMIDES

KW - STEREOCHEMISTRY

U2 - 10.1021/jo800980c

DO - 10.1021/jo800980c

M3 - Article

VL - 73

SP - 5926

EP - 5932

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -