Naphthothiete reaction

Naphthothiazole-2-carboxylic acid decarboxylation, 6, 279 Naphthothiene nomenclature, 1, 21 Naphthothiete, S-methyl-reactions... 

The following compounds have been obtained from thiete 1,1-dioxide Substituted cycloheptatrienes, benzyl o-toluenethiosulfinate, pyrazoles, - naphthothiete 1,1-dioxides, and 3-subst1tuted thietane 1,1-dioxides.It is a dienophile in Diels-Alder reactions and undergoes cycloadditions with enamines, dienamines, and ynamines. Thiete 1,1-dioxide is a source of the novel intermediate, vinylsulfene (CH2=CHCH=SQ2). which undergoes cyclo-additions to strained olefinic double bonds, reacts with phenol to give allyl sulfonate derivatives or cyclizes unimolecularly to give an unsaturated sultene. - Platinum and iron complexes of thiete 1,1-dioxide have been reported. 

Flash vacuum pyrolysis of 2-(l-benzotriazolylmethyl)-l-thionaphthol 483 produces the naphthothiete from which naphtho[l,2-b]thiopyrans are obtained by reaction with dienes (Scheme 172) <1998JHC1505>. 

The sulfur atom of naphthothiete 205 may be methylated with trimethyl-oxonium tetrafluoroborate to give the stable salt. 3-Phenylthiete 213 may be alkylated with trimethyl- or triethyloxonium tetrafluoroborate or the trifluoro-methanesulfonate esters The salts are unstable. Alkylation of 218b with methyl iodide gives a ring-opened product, the reaction being facilitated by electron donation from the iron atom. ... 

The formation of naphthothiete (34) from dithiol 41 and naphthothiadiazine (42) is preceded by biradical intermediate 43 as proven by the photolysis of naphthothiadiazine (42) in carbon disulfide. After 15 min irradiation alongside naphthothiete (34) obtained in a 52% yield there also formed in a 22% yield naphtho[l,8-<7e]-2,4-dihydro-l,3-dithiin-2-thione (44) resulting from the reaction of biradical 43 with carbon disulfide (Scheme 7). 

The reaction of naphthothiete (34) with the lithium aluminum hydride first gives... 

The reaction of naphthosulfone (36, Scheme 11) with the lithium aluminum hydride takes two directions. The first route consists in reduction to naphthothiete (34) with subsequent transformations represented in Scheme 10 (34—>56—>57—>58 59) on quenching dilithium intermediate 57 with water (R = H). The second path involves opening the hetero ring with the nucleophile without reduction (36—>65 67) also analogous to (34 -> -> -> 59) for naphtho[l,8-Z c]thiete proper (cf. Schemes 10 and 11). Methyl naphthyl sulfone (67) thus obtained was also prepared by an independent synthesis by treating naphtho[l,8-Z c]sulfone (36) with methyllithium followed by quenching with water (36 66—>67). 

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