1970
DOI: 10.1002/9780470771242.ch14
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Nitrile oxides

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Cited by 6 publications
(8 citation statements)
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“…A stereospecific reaction was observed in a case with less flexibility. Thus, cycloaddition of acetonitrile oxide [9] to cyclopentadiene [8] gave dihydroisoxazole 19, in which the double bond is specifically attacked from the less hindered side to give one diastereoisomer 20 as the product of the 'until-attack, As mentioned in the introduction and as pointed out by several authors, compounds of the type of 10-18 and 20 represent useful synthons for aminosugars [l] [5] [18], since reduction of the dihydroisoxazole ring produces y -amino alcohols with high degrees of stereoselectivity [3] [6]. Therefore, we briefly investigated the osmylation of some selected derivatives of 1-9.…”
Section: ')mentioning
confidence: 99%
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“…A stereospecific reaction was observed in a case with less flexibility. Thus, cycloaddition of acetonitrile oxide [9] to cyclopentadiene [8] gave dihydroisoxazole 19, in which the double bond is specifically attacked from the less hindered side to give one diastereoisomer 20 as the product of the 'until-attack, As mentioned in the introduction and as pointed out by several authors, compounds of the type of 10-18 and 20 represent useful synthons for aminosugars [l] [5] [18], since reduction of the dihydroisoxazole ring produces y -amino alcohols with high degrees of stereoselectivity [3] [6]. Therefore, we briefly investigated the osmylation of some selected derivatives of 1-9.…”
Section: ')mentioning
confidence: 99%
“…for C,H,,NO (139.20): C 69.03, H 9.41, N 10.06; found: C 69.10, H 9.45, N 10.10. (8). Yield 43 YO, purified by flash chromatography (Et20/hexane 3 :7).…”
Section: Experimental Partmentioning
confidence: 99%
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“…Interestingly, diaryloxadiazoles 9 were also formed upon heating at controlled temperatures in the absence of acetic acid showing that the presence of a carboxylic acid was not critical for the above transformation. Concerning the latest steps of the mechanism for the formation of bis-aryloxadiazoles three possibilities were suggested: i) reaction [7] between arylnitrile and arylnitrile oxide originally formed from 2, ii) reaction [8] of nitrile oxide formed with starting amidoxime, iii) reaction [9] between the nitrile formed and the starting amidoxime. The last mechanism is supported by the fact that diarylfuroxans, always formed by further dimerization of nitrile oxides [10], has not been isolated in the reactions studied.…”
Section: Introductionmentioning
confidence: 99%
“…Ether 0-ketoimines or cyanoacetic esters (5). Morocchi, et al, however, found that the reaction of benzonitrile oxide with acetophenone or propiophenone imines furnished a single product, the 4,5-dihydro-l,2,4-oxadiazoles (6).…”
mentioning
confidence: 99%