e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Application of alkoxy?螃?6??sulfanenitriles as strong alkylating reagents

…, T Fujii, T Dong, Y Wakai, T Yoshimura

Index: Hao, Wei; Fujii, Takayoshi; Dong, Tiaoling; Wakai, Youko; Yoshimura, Toshiaki Heteroatom Chemistry, 2004 , vol. 15, # 3 p. 193 - 198

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Citation Number: 4

Abstract

Abstract Alkoxy-λ 6-sulfanenitriles were found to be versatile alkylating reagents toward various nucleophiles bearing at least one proton such as methanol, phenol, thiophenols, carboxylic acids, p-toluenesulfonic acid, hydrochloric acid, and primary and secondary amines. Reactivity of the alkoxy group of the λ 6-sulfanenitriles showed an opposite trend to the usual SN 2 character, ie Me (1a), Pr (1b), and Bu (1d)≪ i-Pr (1c). In the presence of p- ...

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~0%

2-Chloropropane Structure

2-Chloropropane

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

acetic acid Structure

butyloxy(diphenyl)-λ6-sulfanenitrile Structure

butyloxy(diphen...

~0%

butyl acetate Structure

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

p-Toluenesulfonic acid Structure

p-Toluenesulfon...

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~0%

Isopropyl 4-methylbenzenesulfonate Structure

Isopropyl 4-met...

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

acetic acid Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~0%

Isopropyl acetate Structure

Isopropyl acetate

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Thiophenol Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~0%

ISOPROPYLTHIOBENZENE Structure

ISOPROPYLTHIOBENZENE

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Thiophenol Structure

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~0%

Benzene, (propylthio) Structure

Benzene, (propy...

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Thiophenol Structure

N/A Structure

~0%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Neopentylphenylsulfide Structure

Neopentylphenyl...

Learn More

trifluoroacetic acid Structure

trifluoroacetic acid

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~0%

Acetic acid, 2,2,2-trifluoro-, propyl ester Structure

Acetic acid, 2,...

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

Phenol Structure

~0%

Isopropoxybenzene Structure

Isopropoxybenzene

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

Phenol Structure

~0%

Propoxybenzene Structure

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

butyloxy(diphenyl)-λ6-sulfanenitrile Structure

butyloxy(diphen...

Phenol Structure

~0%

Butoxybenzene Structure

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Piperidine Structure

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~0%

1-propylpiperidine Structure

1-propylpiperidine

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Methanol Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~0%

2-Methoxy Propane Structure

2-Methoxy Propane

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Methanol-d4 Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~0%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

2-(trideuteriomethoxy)propane Structure

2-(trideuteriom...

Learn More

4-Chlorobenzylamine Structure

4-Chlorobenzylamine

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~0%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

N-(4-Chlorobenzyl)-2-propanamine Structure

N-(4-Chlorobenz...

Learn More

Piperidine Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~0%

1-propan-2-ylpiperidine Structure

1-propan-2-ylpi...

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

4-Chlorobenzylamine Structure

4-Chlorobenzylamine

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~0%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

p-chloro-n-propylbenzylamine Structure

p-chloro-n-prop...

Learn More

p-Toluenesulfonic acid Structure

p-Toluenesulfon...

Isopropanol Structure

~86%

Isopropyl 4-methylbenzenesulfonate Structure

Isopropyl 4-met...

Learn More

p-Toluenesulfonic acid Structure

p-Toluenesulfon...

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~96%

Isopropyl 4-methylbenzenesulfonate Structure

Isopropyl 4-met...

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~0%

1-Chloropropane Structure

1-Chloropropane

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

p-Toluenesulfonic acid Structure

p-Toluenesulfon...

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~0%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Propyl 4-methylbenzenesulfonate Structure

Propyl 4-methyl...

Learn More

acetic acid Structure

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~0%

Propyl acetate Structure

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

N/A Structure

~48%

Pivaldehyde Structure

Learn More

Thiophenol Structure

N/A Structure

~95%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Neopentylphenylsulfide Structure

Neopentylphenyl...

Learn More

acetic acid Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~96%

Isopropyl acetate Structure

Isopropyl acetate

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~98%

1-Chloropropane Structure

1-Chloropropane

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

Phenol Structure

~97%

Isopropoxybenzene Structure

Isopropoxybenzene

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

p-Toluenesulfonic acid Structure

p-Toluenesulfon...

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~96%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Propyl 4-methylbenzenesulfonate Structure

Propyl 4-methyl...

Learn More

butyloxy(diphenyl)-λ6-sulfanenitrile Structure

butyloxy(diphen...

Phenol Structure

~90%

Butoxybenzene Structure

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Methanol Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~98%

2-Methoxy Propane Structure

2-Methoxy Propane

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

4-Chlorobenzylamine Structure

4-Chlorobenzylamine

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~92%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

N-(4-Chlorobenzyl)-2-propanamine Structure

N-(4-Chlorobenz...

Learn More

Methanol-d4 Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~99%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

2-(trideuteriomethoxy)propane Structure

2-(trideuteriom...

Learn More

Thiophenol Structure

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~97%

Benzene, (propylthio) Structure

Benzene, (propy...

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

4-Chlorobenzylamine Structure

4-Chlorobenzylamine

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~19%

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

p-chloro-n-propylbenzylamine Structure

p-chloro-n-prop...

Learn More

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

Phenol Structure

~89%

Propoxybenzene Structure

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Piperidine Structure

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~96%

1-propylpiperidine Structure

1-propylpiperidine

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

Piperidine Structure

isopropyloxy(diphenyl)-λ6-sulfanenitrile Structure

isopropyloxy(di...

~67%

1-propan-2-ylpiperidine Structure

1-propan-2-ylpi...

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

acetic acid Structure

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~90%

Propyl acetate Structure

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

trifluoroacetic acid Structure

trifluoroacetic acid

propyloxy(diphenyl)-λ6-sulfanenitrile Structure

propyloxy(diphe...

~96%

Acetic acid, 2,2,2-trifluoro-, propyl ester Structure

Acetic acid, 2,...

Sulfoximine,S,S-diphenyl Structure

Sulfoximine,S,S...

Learn More

First Preparation and Reactions of S, S-Diaryl-S-fluorothiaz...

[Yoshimura, Toshiaki; Kita, Hiroshi; Takeuchi, Kyu; Takata, Eiichi; Hasegawa, Kiyoshi; et al. Chemistry Letters, 1992 , # 8 p. 1433 - 1436]

Synthesis, Structure, and Thermolysis Mechanism of S-Alkoxyt...

[Yoshimura, Toshiaki; Ohkubo, Masanori; Fujii, Takayoshi; Kita, Hiroshi; Wakai, Youko; Ono, Shin; Morita, Hiroyuki; Shimasaki, Choichiro; Horn, Ernst Bulletin of the Chemical Society of Japan, 1998 , vol. 71, # 7 p. 1629 - 1637]

Synthesis, Structure, and Thermolysis Mechanism of S-Alkoxyt...

[Yoshimura, Toshiaki; Ohkubo, Masanori; Fujii, Takayoshi; Kita, Hiroshi; Wakai, Youko; Ono, Shin; Morita, Hiroyuki; Shimasaki, Choichiro; Horn, Ernst Bulletin of the Chemical Society of Japan, 1998 , vol. 71, # 7 p. 1629 - 1637]

Thermolyses and reactions with nucleophiles of N-sulfur-grou...

[Oae, Shigeru; Akutagawa, Kunihiko; Furukawa, Naomichi Phosphorus and Sulfur and the Related Elements, 1984 , vol. 19, p. 223 - 234]

Thermolyses and reactions with nucleophiles of N-sulfur-grou...

[Oae, Shigeru; Akutagawa, Kunihiko; Furukawa, Naomichi Phosphorus and Sulfur and the Related Elements, 1984 , vol. 19, p. 223 - 234]