Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane
Тип публикации: Journal Article
Дата публикации: 1973-04-25
scimago Q2
wos Q3
БС2
SJR: 0.491
CiteScore: 3.0
Impact factor: 1.8
ISSN: 0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Краткое описание
The addition of dichlorocarbene (generated by the interaction of sodium methoxide and ethyl trichloroacetate) to bicyclo[3.2.1]oct-2-ene, its 3-chloro and exo-3,4-dichloro derivatives gives the exo 1 : 1 adducts in yields of 94, 89 and 48%. By suitable chemical reactions of these adducts, convenient syntheses of bicyclo[4.2.1]nona-2,4-diene and bicyclo[4.2.1]non-3-ene, together with their monochloro, dichloro and trichloro derivatives are obtained. Bicyclo[4.2.1]-nonan-3-one is also obtained from bicyclo[4.2.1]non-3-ene in a synthesis starting from the readily available 5-hydroxymethylnorborn-2-ene in an overall yield of 20%.
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Jefford C. W., Burger U., Delay F. Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane // Helvetica Chimica Acta. 1973. Vol. 56. No. 3. pp. 1083-1096.
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Jefford C. W., Burger U., Delay F. Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane // Helvetica Chimica Acta. 1973. Vol. 56. No. 3. pp. 1083-1096.
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TY - JOUR
DO - 10.1002/hlca.19730560329
UR - https://doi.org/10.1002/hlca.19730560329
TI - Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane
T2 - Helvetica Chimica Acta
AU - Jefford, Charles W.
AU - Burger, Ulrich
AU - Delay, Franois
PY - 1973
DA - 1973/04/25
PB - Wiley
SP - 1083-1096
IS - 3
VL - 56
SN - 0018-019X
SN - 1522-2675
ER -
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BibTex (до 50 авторов)
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@article{1973_Jefford,
author = {Charles W. Jefford and Ulrich Burger and Franois Delay},
title = {Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane},
journal = {Helvetica Chimica Acta},
year = {1973},
volume = {56},
publisher = {Wiley},
month = {apr},
url = {https://doi.org/10.1002/hlca.19730560329},
number = {3},
pages = {1083--1096},
doi = {10.1002/hlca.19730560329}
}
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MLA
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Jefford, Charles W., et al. “Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane.” Helvetica Chimica Acta, vol. 56, no. 3, Apr. 1973, pp. 1083-1096. https://doi.org/10.1002/hlca.19730560329.