Organic Syntheses 2003
DOI: 10.1002/0471264180.os049.19
|View full text |Cite
|
Sign up to set email alerts
|

Diphenylcarbodiimide, Method II

Abstract: Diphenylcarbodiimide, Method II intermediate: N‐sulfinylaniline reactant: 50 g. (0.41 mole) of benzaldoxime solvent: 150 ml. of petroleum ether intermediate: benzohydroxamoyl chloride intermediate: triethylamine hydrochloride product: diphen… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1
1

Citation Types

0
11
0

Year Published

2006
2006
2024
2024

Publication Types

Select...
2
2

Relationship

0
4

Authors

Journals

citations
Cited by 4 publications
(11 citation statements)
references
References 9 publications
0
11
0
Order By: Relevance
“…Thus, it is hypothesized that the PhNSO compound formerly obtained in 14–18% yield in benzene is a product of the parallel reaction (B) and not the unreacted reagent. 48 It should be noted that upon changing the solvent from benzene to diethyl ether, the reagents are not purified from the final reaction mixture. 47 These observations are consistent with the results of in silico investigations: barrier heights of the first reaction steps (determining the ratio of the final product) in the pathways (A) and (B) are predicted to differ by 1.5 and 2.2 kcal mol −1 for reactions in benzene and in THF, respectively.…”
Section: Resultsmentioning
confidence: 99%
See 3 more Smart Citations
“…Thus, it is hypothesized that the PhNSO compound formerly obtained in 14–18% yield in benzene is a product of the parallel reaction (B) and not the unreacted reagent. 48 It should be noted that upon changing the solvent from benzene to diethyl ether, the reagents are not purified from the final reaction mixture. 47 These observations are consistent with the results of in silico investigations: barrier heights of the first reaction steps (determining the ratio of the final product) in the pathways (A) and (B) are predicted to differ by 1.5 and 2.2 kcal mol −1 for reactions in benzene and in THF, respectively.…”
Section: Resultsmentioning
confidence: 99%
“…The PhNSO-catalyzed conversion PhCNO -PhNCO is also a possible but less favorable reaction pathway, and it explains the found traces of PhNCO in the reaction mixture. 47,48 In the end, we also surveyed the effect of phenyl ring substituents on the reaction kinetics. It turns out that such a substitution slows down the reaction with respect to the unsubstituted PhCNO.…”
Section: Discussionmentioning
confidence: 99%
See 2 more Smart Citations
“…Chloride (4) A solution of p-nitro benzaldoxime (0.332 g, 0.002 mol) in dimethyl formarmide (5 cm 3 ) was transferred to a 100 cm 3 round-bottom flask equipped with a guard tube, and n-chlorosuccinimide (0.332 g, 0.0024 mol) was added to it in small portions with vigorous stirring. The stirring was continued overnight.…”
Section: Preparation Of 4-nitrobenzohydroxamoylmentioning
confidence: 99%