Isomeric Alkyl Derivatives of Thiosaccharin (2,3-Dihydro-3-Thiobenzisosulfonazole)

Meadow, J. R.; Cavagnol, J. C.

doi:10.1021/jo50004a014

Cited by 25 publications

(9 citation statements)

References 5 publications

(5 reference statements)

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“…Benzisothiazoline (Hbit), sodium saccharinate (Nasac) and 2-amino-3methylpyridine (ampy) are commercial products used as received. [Pd(Me 2 NCH 2 C 6 H 4 - [27], 2-acetylamino-3-methylpyridine (acmpy) [38], thiosaccharin (Htsac) [39] and sodium benzisothiozolinate (Nabit) [19] were prepared by literature methods.…”

Section: General Methods Reagents and Instrumentationmentioning

confidence: 99%

A comparative study of the coordination of saccharinate, thiosaccharinate and benzisothiozolinate ligands to cyclometalated [Pd(Me2NCH2C6H4-κN,C)(μ-Cl)]2: Molecular structures of [Pd(Me2NCH2C6H4-κN,C)(µ-X)]2 (X = sac, bit and tsac) and [Pd(Me2NCH2C6H4-κN,C)Cl(ampyH-κN)] (ampyH = 2-amino-3-methylpyridine)

Al‐Jibori

Hameed

Al‐Janabi

et al. 2018

Inorganica Chimica Acta

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Section: General Methods Reagents and Instrumentationmentioning

confidence: 99%

A comparative study of the coordination of saccharinate, thiosaccharinate and benzisothiozolinate ligands to cyclometalated [Pd(Me2NCH2C6H4-κN,C)(μ-Cl)]2: Molecular structures of [Pd(Me2NCH2C6H4-κN,C)(µ-X)]2 (X = sac, bit and tsac) and [Pd(Me2NCH2C6H4-κN,C)Cl(ampyH-κN)] (ampyH = 2-amino-3-methylpyridine)

Al‐Jibori

Hameed

Al‐Janabi

et al. 2018

Inorganica Chimica Acta

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“…Na 2 PdCl 4 , benzisothiazolinone (Hbit), benzylamine and sodium saccharinate were purchased and used as received. Thiosaccharin [27] …”

Section: Methodsmentioning

confidence: 99%

A comparative study of the coordination of saccharinate (sac), thiosaccharinate (tsac) and benzisothiazolinate (bit) ligands to trans-[PdCl2(H2NBz)2]: molecular structure of cis-[Pd(bit)2(H2NBz)2]

et al. 2016

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A comparative study of reactions of saccharinate (sac), thiosaccharinate (tsac) and benzisothiozolinate (bit) with trans-[PdCl 2 (H 2 NBz) 2 ] is reported. While in all cases substitution of both chlorides occurs, product types differ for the three closely related ligands. With sodium saccharinate, trans-[Pd(N-sac) 2 (H 2 NBz) 2 ] results in which the sac ligands are N-bound. A similar N-bound coordination is observed with sodium benzisothiazolinate, but a crystal structure shows that they adopt a mutual cis arrangement in cis-[Pd(N-bit) 2 (H 2 NBz) 2 ]. In contrast, with sodium thiosaccharinate it is proposed that the new ligands adopt an S-bound coordination mode in trans-[Pd(S-tsac) 2 (H 2 NBz) 2 ].

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“…Na 2 [PdCl 4 ], benzisothiazolinone (Hbit), 2-aminothiazole, 2-aminobenzothiazole (abzt), 2-aminopyridine (apy), 2-amino-3-methylpyridine (ampy), 2-aminopyrimidine, 2-amino-5-methyl-1,3,4-thiazole, 2,6-diaminopyridine (dapy) were purchased and used as supplied. Thiosaccharine (Htsac) [11], 2-acetylaminothiazole (actz) [12], 2-acetylaminobenzothiazole (acbzt) [12], 2-acetylamino-3-methylpyridine (acmpy) [12], 2-acetylaminopyrimidine (acpym) [13], 2-acetylamino-5-methyl-1,3,4-thiadiazole (acmtd) [14] and 2,6-diacetylaminopyridine (dacpy) [15] were prepared by literature methods.…”

Section: General Methods Reagents and Instrumentationmentioning

confidence: 99%

Palladium(II) benzisothiazolinate (bit) complexes with amino-, acetylamino-, heterocyclic and phosphine co-ligands. Crystal structure of [Pd(bit)2(κ2-dppe)]·2EtOH

Al‐Jibori

Ahmed

et al. 2015

Inorganica Chimica Acta

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a b s t r a c tA series of square-planar palladium(II) benzisothiazolinate (bit) of the general type [Pd(bit) 2 L 2 ] have been prepared and characterized by analytical and spectroscopic methods. Two synthetic routes have been employed, namely reactions of [Pd(bit) 2 ]ÁH 2 O with two equivalents of ligands (L = amine, amide, phosphine) or nucleophile displacement of chloride by benzisothiazolinate starting from trans-[PdCl 2 L 2 ]. Both routes afford the new complexes in good yields as easily isolated, air and moisture stable, colored solids. The precursor, [Pd(bit) 2 ]ÁH 2 O, is itself prepared in high yields upon reaction of Na[bit] with Na 2 [PdCl 4 ] in methanol and the analogous platinum complex, [Pt(bit) 2 ]ÁH 2 O, is similarly prepared from K 2 [PtCl 4 ]. It is not clear if these species are mono-or dimeric, and formulation as [M 2 (l-bit) 4 (H 2 O) 2 ] with the four benzisothiazolinate spanning the metal-metal vector and possibly binding through coordination of nitrogen and oxygen is suggested. Diphosphine adducts, cis-[Pd(bit) 2 {j 2 -Ph 2 P(CH 2 ) n PPh 2 }] (n = 1-4) can be prepared both upon addition of the diphosphine to [Pd(bit) 2 ]ÁH 2 O and from reactions of cis-[PdCl 2 {j 2 -Ph 2 P(CH 2 ) n PPh 2 }] with two equivalents of Na [bit]. A crystal structure of cis-[Pd(bit) 2 (j 2 -dppe)] reveals that the benzisothiazolinate ligands are bonded in a monodentate fashion through nitrogen and this binding mode is proposed for all [Pd(bit) 2 L 2 ] and [Pd(bit) 2 L] complexes. With dppb (n = 4) a second product is seen by NMR spectroscopy being proposed to be the part-substituted complex cis-[PdCl(bit)(j 2 -dppb)], while with dppm (n = 1) two further products are seen spectroscopically, proposed as trans-[Pd(bit) 2 (j 1 -dppm) 2 ] and (more tenuously) [Pd 2 (bit) 4 (dppm) 2 ]. The former is also prepared in good yields from reaction of [Pd(j 2 -dppm) 2 ]Cl 2 with Na [bit]. These studies show that palladium benzisothiazolinate are easily accessed and show good air and moisture stability.

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Isomeric Alkyl Derivatives of Thiosaccharin (2,3-Dihydro-3-Thiobenzisosulfonazole)

Cited by 25 publications

References 5 publications

A comparative study of the coordination of saccharinate (sac), thiosaccharinate (tsac) and benzisothiazolinate (bit) ligands to trans-[PdCl2(H2NBz)2]: molecular structure of cis-[Pd(bit)2(H2NBz)2]

Palladium(II) benzisothiazolinate (bit) complexes with amino-, acetylamino-, heterocyclic and phosphine co-ligands. Crystal structure of [Pd(bit)2(κ2-dppe)]·2EtOH

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