Cyclizations of Enolates onto Aromatic Rings via the Photo-SRN1 Reaction. Preparative and echanistic Aspects

M. F. Semmelhack; Thomas M. Bargar

doi:10.1021/jo00428a056

Cyclizations of Enolates onto Aromatic Rings via the Photo-SRN1 Reaction. Preparative and echanistic Aspects

M. F. Semmelhack, Thomas M. Bargar

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

55 Scopus citations

Abstract

Six-, seven-, eight-, and ten-membered rings are obtained by photostimulated aromatic nucleophilic substitution by enolate anions, but only when internal H-atom transfer from the 7 position of the ketone is blocked, as shown by deuterium labeling.

Original language	English (US)
Pages (from-to)	1481-1482
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	42
Issue number	8
DOIs	https://doi.org/10.1021/jo00428a056
State	Published - 1977
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00428a056

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@article{cc5c7e66a2784690a4b8c8e75e7ba03b,

title = "Cyclizations of Enolates onto Aromatic Rings via the Photo-SRN1 Reaction. Preparative and echanistic Aspects",

abstract = "Six-, seven-, eight-, and ten-membered rings are obtained by photostimulated aromatic nucleophilic substitution by enolate anions, but only when internal H-atom transfer from the 7 position of the ketone is blocked, as shown by deuterium labeling.",

author = "Semmelhack, {M. F.} and Bargar, {Thomas M.}",

year = "1977",

doi = "10.1021/jo00428a056",

language = "English (US)",

volume = "42",

pages = "1481--1482",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Cyclizations of Enolates onto Aromatic Rings via the Photo-SRN1 Reaction. Preparative and echanistic Aspects

AU - Semmelhack, M. F.

AU - Bargar, Thomas M.

PY - 1977

Y1 - 1977

N2 - Six-, seven-, eight-, and ten-membered rings are obtained by photostimulated aromatic nucleophilic substitution by enolate anions, but only when internal H-atom transfer from the 7 position of the ketone is blocked, as shown by deuterium labeling.

AB - Six-, seven-, eight-, and ten-membered rings are obtained by photostimulated aromatic nucleophilic substitution by enolate anions, but only when internal H-atom transfer from the 7 position of the ketone is blocked, as shown by deuterium labeling.

UR - http://www.scopus.com/inward/record.url?scp=0000633067&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000633067&partnerID=8YFLogxK

U2 - 10.1021/jo00428a056

DO - 10.1021/jo00428a056

M3 - Letter

AN - SCOPUS:0000633067

SN - 0022-3263

VL - 42

SP - 1481

EP - 1482

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Cyclizations of Enolates onto Aromatic Rings via the Photo-SRN1 Reaction. Preparative and echanistic Aspects

Abstract

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