volume 56 issue 3 pages 1083-1096

Synthesis of Bridged Bicyclic Molecules using Halocarbenes. Derivatives of bicyclo[4.2.1]nonane

Publication typeJournal Article
Publication date1973-04-25
scimago Q2
wos Q3
SJR0.491
CiteScore3.0
Impact factor1.8
ISSN0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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MLA Copy
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.