5-Allylthio

Conversion of 5-allylthioimidates into /V-allylthioamides is catalyzed by Pd(Il). 2-Allylthiopyridine (820) is converted into the less stable l-allyl-2-thio-pyridone 821 owing to Pd complex formation[509], Claisen rearrangement of 2-(allylthio)pyrimidin-4-(3//)-one (822) affords the A-l-allylation product 823 as the main product rather than the A -3-allylation product 824[510] The smooth rearrangement of the allylic thionobenzoate 825 to the allyl thiolo-benzoate 826 is catalyzed by both PdCl2(PhCN)2 and Pd(Ph3P)4 by different mechanisms[511],... 

General Procedures for the Reaction of 2-Allyloxy- (or 2-Allylthio)benzothiazole Derivatives with Organocop-per Reagents42 ... 

A. 2-Allylthio-2-thiazoline [Thiazole, 4,5-dihydro-2-(2-propenyltliio)-]. A solution of 11.9 g. (0.100 mole) of 2-mercapto-2-thiazoline [2-Thiazoli-dinethione] (Note 1) in 00 ml. of tetrahydrofuran is prepared in a 200-ml., one-necked, round-bottomed flask fitted with a 25-ml.,... 

Cyclohexadiene-l, 4-dione, 2-(phenylmethyl)-], 70 Benzothiazole, 2-(allylthio)- [Benzothia-... 

This reaction is applicable to a dithienotropone synthesis starting from tropone 2,7-bis(thioether). An earlier attempt at rearrangement of 2-(allylthio)tropone with xylene as solvent failed (59MI2). 

Mercapto-benzimidazol wird von Allyl-bromid in Gegenwart von Natriumhydrogencarbonat zunachst am S-Atom zu 2-Allylthio-benzimidazol (60%) alkyliert. Beim Erwarmen wandert der Allyl-Rest (Claisen-Umlagerung) vom S- zum N-Atom, und man erhiilt l-Allyl-2-mer-capto-benzimidazol (50% Schmp. 115—117°)372. 

Thiazolidine-2-thione, 3-allyl-, 56, 79 2-Thiazohne, 2-allylthio-, 56, 77 2-Thiazoline, 2-benzylthio-, 56, 82 2-Thiazoline, 2-cmnamylthio-, 56, 82 2 Thiazoline, 2 ethylthio, 56, 82 2-Thiazohne 2-mercapto-, 56, 77 2-Thiazoline, 2-methylthio-, 56, 82 2-Thiazohne, 2-(4-phenyl-l-buten-3-yl)-thio-, 56, 78... 

The 3-phenylthieno[2,3-d]pyrimidine-2,4-diones 3b and the corresponding -4-one-2-thiones 4b were converted into the respective 2-allyloxy 139a and 2-allylthio 139b derivatives by reaction with allyl chloride in base (89KGS347). 

Pyrimidin 2-Allylthio-4-(pentafluor-ethyl)-4-hydroxy-l (3),4,5,6-tetrahydro- E14a/2, 459 (En-on + Amidin)... 

These reactions, coupl with the alkylations of sulfides and selenides, allow the homologation of primary alkyl halides - - - and the transformation of allyl halides to homoallyl halides. A related process, employing 2-methylthio- and 2-allylthio-thiazoline, allows the iodomeAylation (ICH2—) and the iodopropenylation (ICH2CH=CH—) of alkyl halides (Scheme 54).i3iii,i32.i7i... 

Heterocyclization of 2-(allylthio, propargylthio)thieno[2,3-<7]pyrimidin-4-ones 202 with phenylselenenyl halides yielded thieno[3/,2, 5,6]pyrimido[2,l-Z>][l,4,3]thiaselena-zinium halides 203 (2002UKZ43, 2002UKZ111). 

Allylthio-l,3-benzothiazol ergibt bei der Bromierung 3-Brom-3,4-dihydro-2H-(l,3-thiazinio [2,3-b]-l, 3-benzothiazolium)-bromid386 ... 

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