1963
DOI: 10.1039/jr9630000826
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154. Interaction of boron chlorides and esters of sulphonic acids

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Cited by 12 publications
(11 citation statements)
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“…In another experiment with more trimethylamine the proportion of 2 did not appear to increase but rather the starting material diminished and peaks showing the presence of 1 and tetramethylammonium cation appeared. Route (b) is probably of limited use as a procedure for isolating [Olbetylates, but these experiments serve to confirm the original suggestion of Charalambous et al (16) …”
supporting
confidence: 75%
See 1 more Smart Citation
“…In another experiment with more trimethylamine the proportion of 2 did not appear to increase but rather the starting material diminished and peaks showing the presence of 1 and tetramethylammonium cation appeared. Route (b) is probably of limited use as a procedure for isolating [Olbetylates, but these experiments serve to confirm the original suggestion of Charalambous et al (16) …”
supporting
confidence: 75%
“…Charalambous et al (16) used pyridine for most of these experiments and it might be momentarily surprising to note that we saw little or no reaction in an nmr experiment with phenyl chlorosulfate and pyridine in carbon tetrachloride. This observation does not preclude reaction of pyridine with phenyl chlorosulfate, but does require that if such reaction occurs, the equilibrium constant must strongly favour the starting materials.…”
mentioning
confidence: 99%
“…In light of this, the more reactive 4-nitrophenyl sulfamate 6 was prepared by treating the 3Aamine 3 with 4-nitrophenyl chlorosulfate 4. 9 Coupling of 6 with 5A-alcohol 8 was successful resulting in the sulfamate dinucleoside 11 in excellent yield at room temperature. Similarly the sulfamide dinucleoside 9 could also be prepared more effectively at room temperature from 6 and the 5A-amine 7.…”
mentioning
confidence: 99%
“…4‐Nitrophenyl chlorosulfate 18.1 was prepared for the preparation of chiral non‐symmetric sulfamides (Scheme 18). [62] Addition of sulfuryl chloride to 4‐nitrophenol led to the construction of 18.1 in 83 % as a stable crystalline solid [63] . 18.1 was then treated with amine 18.2 at room temperature or −78 °C to afford the symmetrical sulfamide 18.3 as the major product and 4‐nitrophenyl sulfamate 18.5 as a minor product, with none of the sulfamoyl chloride 18.4 being isolated.…”
Section: Methods To Generate Acyclic Sulfamidesmentioning
confidence: 99%
“…[62] Addition of sulfuryl chloride to 4-nitrophenol led to the construction of 18.1 in 83 % as a stable crystalline solid. [63] 18.1 was then treated with amine 18.2 at room temperature or À 78°C to afford the symmetrical sulfamide 18.3 as the major product and 4-nitrophenyl sulfamate 18.5 as a minor product, with none of the sulfamoyl chloride 18.4 being isolated. The mechanism of nucleophilic substitution reaction of 18.1 includes nucleophilic attack at sulfur with either SÀ Cl or SÀ OAr bond scission with the SÀ OAr bond cleavage being the major reaction pathway.…”
Section: -Nitrophenyl Chlorosulfatementioning
confidence: 99%