1967
DOI: 10.1139/v67-372
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The addition of "bromine fluoride" to norbornene

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1969
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Cited by 14 publications
(7 citation statements)
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“…The product ratios did change when some of the crude reaction mixtures were at room temperature overnight. However, isolated products were stable to the reaction conditions and VPC analysis except for the 1,4-product (20) from the diene 7 which decomposes.…”
Section: Methodsmentioning
confidence: 96%
See 1 more Smart Citation
“…The product ratios did change when some of the crude reaction mixtures were at room temperature overnight. However, isolated products were stable to the reaction conditions and VPC analysis except for the 1,4-product (20) from the diene 7 which decomposes.…”
Section: Methodsmentioning
confidence: 96%
“…The two peaks gave almost identical mass spectral fragments and are the E and Z isomers of 18. The important mass spectral peaks were m/e (relative intensity) C3H5+ 41 (100), CH2=0+CH3 45 (71), and P -HF 112 (20). Chemical ionization mass spectrometry gave base peaks m/e 113 for 17, 18, and 21 via the following pathway: Norbornene (8) reacts with 1 to give difluoro-, fluoromethoxy-, and nortricyclane products.…”
mentioning
confidence: 96%
“…In the course of a study of the reaction of "bromine fluoride" (N-bromoacetamide + hydrogen fluoride) with norbornene (I), it was found that the major dihalo products were 7-syn-bromo-2-exo-fluoronorbornane (3) and 7-anti-bromo-2-exo-fluoronorbornane (4), (Scheme 1) (1,2). Since the ionic reaction of either "bromine fluoride" or bromine with norbornene would presumably lead to the same first intermediate, the 7-anti-isomer 4 was unexpected on the basis of the reported bromination of norbornene (3)(4)(5), from which the only dibromo products identified were 7-syn,2-exo-dibromonorbornane (19) and 2-exo,3-endo-dibromonorbornane bromides), no further report has been published.…”
Section: Introductionmentioning
confidence: 99%
“…(w,,,-4Hz) is characteristic of a proton on C-7 bearing bromine. (2). The position and three line pattern of the peak at 3.93 p.p.m.…”
Section: Introductionmentioning
confidence: 99%
“…1,8-Dimethylnaphthalene gave only the -lithio derivative, even when it was treated for prolonged periods with a large excess of BuLi,6 whereas with namylsodium-TMEDA the , '-disodio derivative was produced quantitatively.7 Other isomers, such as 1,2-, 1,3and 1,6-dimethylnaphthalene (and o-and m-xylene), also formed , '-disodio derivatives, but 1,4-dimethylnaphthalene (and p-xylene) was only monometalated. A reasonable explanation for the relative reactivities of the (6) Kershner, G. D.; Gaidis, J. A.; Freedman, .…”
mentioning
confidence: 98%