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

CHEMISTRY OF CIS-AND TRANS-9-PHENYLSELENOXANTHENE-N-ARYLSULFONYLSELENILIMINES1

K Tomimatsu, T Kataoka, H Shimizu…

Index: Tomimatsu, Kiminori; Kataoka, Tadashi; Shimizu, Hiroshi; Hori, Mikio Phosphorus and Sulfur and the Related Elements, 1983 , vol. 16, p. 97 - 110

Full Text: HTML

Citation Number: 5

Abstract

Abstract cis-and trans-9-Phenylselenoxanthene-N-(arylsulfonyl) selenilimines were synthesized and isolated. Their stereochemistry was ascertained from the NMR spectra. Cis isomers reacted with chloramine-T or-B by an SN 2 type substitution to form trans isomers, but the reverse reaction did not take place. When trans isomers were refluxed in toluene they underwent intermolecular 1, 4 rearrangement to give 9-arylsulfonamido-9- ...

phenyl[o-(phenylseleno)phenyl]methanol Structure

phenyl[o-(pheny...

~10%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

1-benzhydryl-2-[(2-benzhydrylphenyl)diselanyl]benzene Structure

1-benzhydryl-2-...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

1-benzhydryl-2-[(2-benzhydrylphenyl)diselanyl]benzene Structure

1-benzhydryl-2-...

2-phenylselanylbenzaldehyde Structure

2-phenylselanyl...

~%

1-benzhydryl-2-[(2-benzhydrylphenyl)diselanyl]benzene Structure

1-benzhydryl-2-...

trans-9-Phenylselenoxanthene-N-(p-toluenesulfonyl)selenilimine Structure

trans-9-Phenyls...

~84%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

phenyl[o-(phenylseleno)phenyl]methanol Structure

phenyl[o-(pheny...

~81%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

1-benzhydryl-2-[(2-benzhydrylphenyl)diselanyl]benzene Structure

1-benzhydryl-2-...

METHYLMAGNESIUM IODIDE Structure

METHYLMAGNESIUM...

trans-9-Phenylselenoxanthene-N-(p-toluenesulfonyl)selenilimine Structure

trans-9-Phenyls...

~82%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

N/A Structure

trans-9-Phenylselenoxanthene-N-(benzenesulfonyl)selenilimine Structure

trans-9-Phenyls...

~%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

Sodium benzeneselenolate Structure

Sodium benzenes...

~%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

2-phenylselanylbenzaldehyde Structure

2-phenylselanyl...

~%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

trans-9-Phenylselenoxanthene-N-(p-toluenesulfonyl)selenilimine Structure

trans-9-Phenyls...

4-Anisylmagnesium bromide Structure

4-Anisylmagnesi...

~30%

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

9-(p-methoxyphenyl)-9-phenylselenoxanthene Structure

9-(p-methoxyphe...

(2,5-Dichlorophenyl)(phenyl)methanone Structure

(2,5-Dichloroph...

Sodium benzeneselenolate Structure

Sodium benzenes...

~97%

(5-chloro-2-phenylselanylphenyl)-phenylmethanone Structure

(5-chloro-2-phe...

(2,5-Dichlorophenyl)(phenyl)methanone Structure

(2,5-Dichloroph...

~%

2-chloro-9-phenyl-9H-selenoxanthene Structure

2-chloro-9-phen...

Sodium benzeneselenolate Structure

Sodium benzenes...

~%

2-chloro-9-phenyl-9H-selenoxanthene Structure

2-chloro-9-phen...

(5-chloro-2-phenylselanylphenyl)-phenylmethanone Structure

(5-chloro-2-phe...

~%

2-chloro-9-phenyl-9H-selenoxanthene Structure

2-chloro-9-phen...

trans-9-Phenylselenoxanthene-N-(benzenesulfonyl)selenilimine Structure

trans-9-Phenyls...

~%

4-methyl-N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

4-methyl-N-(9-p...

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

~%

4-methyl-N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

4-methyl-N-(9-p...

Sodium benzeneselenolate Structure

Sodium benzenes...

~%

4-methyl-N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

4-methyl-N-(9-p...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

4-methyl-N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

4-methyl-N-(9-p...

2-phenylselanylbenzaldehyde Structure

2-phenylselanyl...

~%

4-methyl-N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

4-methyl-N-(9-p...

phenyl[o-(phenylseleno)phenyl]methanol Structure

phenyl[o-(pheny...

~%

4-methyl-N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

4-methyl-N-(9-p...

Chloramine-T Structure

~%

4-methyl-N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

4-methyl-N-(9-p...

Sodium chloro(phenylsulfonyl)azanide Structure

Sodium chloro(p...

~%

4-methyl-N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

4-methyl-N-(9-p...

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

9-pentadeuteriophenylselenoxanthene Structure

9-pentadeuterio...

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

trans-9-Phenylselenoxanthene-N-(p-toluenesulfonyl)selenilimine Structure

trans-9-Phenyls...

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

Sodium benzeneselenolate Structure

Sodium benzenes...

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

2-phenylselanylbenzaldehyde Structure

2-phenylselanyl...

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

phenyl[o-(phenylseleno)phenyl]methanol Structure

phenyl[o-(pheny...

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

2-(phenylseleno)phenylpentadeuteriophenylmethanol Structure

2-(phenylseleno...

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

Sodium chloro(phenylsulfonyl)azanide Structure

Sodium chloro(p...

~%

N-(9-phenylselenoxanthen-9-yl)benzenesulfonamide Structure

N-(9-phenylsele...

9-phenyl-9H-selenoxanthene Structure

9-phenyl-9H-sel...

~%

9-methoxy-9-phenylselenoxanthene Structure

9-methoxy-9-phe...

trans-9-Phenylselenoxanthene-N-(benzenesulfonyl)selenilimine Structure

trans-9-Phenyls...

~%

9-methoxy-9-phenylselenoxanthene Structure

9-methoxy-9-phe...

trans-9-Phenylselenoxanthene-N-(p-toluenesulfonyl)selenilimine Structure

trans-9-Phenyls...

~%

9-methoxy-9-phenylselenoxanthene Structure

9-methoxy-9-phe...

Sodium benzeneselenolate Structure

Sodium benzenes...

~%

9-methoxy-9-phenylselenoxanthene Structure

9-methoxy-9-phe...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

9-methoxy-9-phenylselenoxanthene Structure

9-methoxy-9-phe...

2-phenylselanylbenzaldehyde Structure

2-phenylselanyl...

~%

9-methoxy-9-phenylselenoxanthene Structure

9-methoxy-9-phe...

phenyl[o-(phenylseleno)phenyl]methanol Structure

phenyl[o-(pheny...

~%

9-methoxy-9-phenylselenoxanthene Structure

9-methoxy-9-phe...

Methanol Structure

trans-9-phenylselenoxanthene 10-oxide Structure

trans-9-phenyls...

~59%

9-methoxy-9-phenylselenoxanthene Structure

9-methoxy-9-phe...

N/A Structure

Sodium benzeneselenolate Structure

Sodium benzenes...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~84%

2-phenylselanylbenzaldehyde Structure

2-phenylselanyl...