7,7,9,9-Tetramethyl-8-thiosulphinyliminothio-1,4-dioxa-8-azaspiro[4,5]decane

Tamura, Chihiro; Aiba, K.; Satô, Shirô; Hata, Tadashi; Morimura, S.; Yoshioka, T.

doi:10.1107/s0567740877012448

Cited by 8 publications

(2 citation statements)

References 7 publications

(9 reference statements)

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“…The cis conformation of S,N-(Scheme IV) is predicted to be more stable than the truns, in agreement with the reported structures of several RS3N derivatives (SO. 112,222,223). The energetic preference for the cis isomer has been suggested to arise from weak Coulombic interactions between the 1,4 sulfurs.…”

Section: Self-consistent Field (Scf) Culculutionsmentioning

confidence: 99%

Cyclic and Heterocyclic Thiazenes

Oakley

1988

Progress in Inorganic Chemistry

126

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Scheme I1A second binary compound, tetrasulfur dinitride (S4N2, 4), was also isolated before the end of the last century (32). Its correct elemental composition, however, was not established until 1925 (33), and its molecular formula not confirmed until 1951 (34). Early estimates suggested the formula N2Sj (32), an observation that attests to the tendency of the molecule to disproportionate above its melting point of 22.5"C (hence, the high sulfur content). The six-membered ring structure with a half-chair conformation was finally confirmed in 1981 (35,36). Most early preparative methods involved a thermal decomposition, for example, of S4N, in the presence of sulfur and/or carbon disulfide (37,38). More recently the use of simple metathetical reactions, for example, between Ni(S2N2H)? and S2CI2 has been explored (39). A simple procedure involving the reaction of aqueous ammonia with sulfur monochloride has also been developed (40); although the yield is low (<2%), the method provides a convenient preparation of small quantities (<0.5 g) starting from commercially available materials (3%). The solid state polymerization of S4N2 to (SN), ( 5 ) has recently been reported (36); this process is presumably initiated by trace amounts of (radical) impurities since, when recrystallized from diethyl ether, solid S,N, is indefinitely stable below its melting point (3%).Disulfur dinitride (6) (Scheme 11) was first generated (inadvertently) by Burt in 1910 (41) during an attempt to remove sulfur impurities from SJNJ by passing a vaporous mixture of the two over finely divided silver. At the time he noted the formation of a blue film [later characterized as (SN), polymer]. This reaction has been studied extensively since then, and now 304 RICHARD T. OAKLEY

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Section: Self-consistent Field (Scf) Culculutionsmentioning

confidence: 99%

Cyclic and Heterocyclic Thiazenes

Oakley

1988

Progress in Inorganic Chemistry

126

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“…well represented by the thiosulfine isomeric or resonance forms(169)(170)(171)(172)(173)(174)(175)(176).Thiosulfine intermediates 178 may also be involved in the formation of the dithiadiazapentalenes 179 from the reaction of disulfur dichloride (or sulfur dichloride)with the dioximes177.151 Thiosulfine (178) intermediacy in the reaction of 177 with sulfur dichloride may -HgO 179 be rationalized in terms of initial thione formation and subsequent combination with SC12.152 Recently thiosulfines 183 have been proposed154 as intermediates in the reaction of morpholine with the disulfides 180. A likely pathway to 183 involves the…”

mentioning

confidence: 99%

Compounds containing the sulfur-sulfur double bond

Kutney¹,

Turnbull²

1982

Chem. Rev.

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The Chemistry of the Thiosulfinyl Group: Preparation, Structure, and Spectroscopic and Chemical Properties of Cyclic Thionosulfites

Nakayama¹,

Yoshida²,

Sugihara³

et al. 2005

Helvetica Chimica Acta

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Treatment of the tetrahydrothiophene‐3,4‐diol 5 with 1,1′‐thiobis‐(1H‐benzimidazole) (6) furnished two diastereoisomers of the novel cyclic thionosulfite 4 with different configurations at the pseudo‐tetrahedral center of the thiosulfinyl (SS) group. The configuration of the SS group of the major diastereoisomer (isolated in 45% yield) was established to be syn to the thiolane ring, as determined by X‐ray crystallographic analysis, while that of the minor diastereoisomer (isolated in 10% yield) was anti. 1H‐NMR Spectroscopic analysis clarified that the shielding and deshielding zones of the SS group are similar to those of the well‐documented SO group. Characteristic absorptions of the SS group in the IR, Raman, and UV/VIS spectra were assigned on the basis of calculations at the B3LYP/6‐31G* level. The reactivity of the SS group toward thermolysis, hydrolysis, and oxidation was examined. The SS group is more resistant toward oxidation than the divalent sulfide S‐atom, but is oxidatively converted to the SO group.

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7,7,9,9-Tetramethyl-8-thiosulphinyliminothio-1,4-dioxa-8-azaspiro[4,5]decane

Cited by 8 publications

References 7 publications

Cyclic and Heterocyclic Thiazenes

Cyclic and Heterocyclic Thiazenes

Compounds containing the sulfur-sulfur double bond

The Chemistry of the Thiosulfinyl Group: Preparation, Structure, and Spectroscopic and Chemical Properties of Cyclic Thionosulfites

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