First isolable dithiiranes: 3-(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-3-phenyldithiirane 1-oxides

Ishii, Akihiko; Akazawa, Toru; Ding, Meng; Honjo, Takanari; Nakayama, Juzo; Hoshino, Minoru; Shiro, Motoo

doi:10.1021/ja00064a072

Cited by 48 publications

(5 citation statements)

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“…(2) When phenyl vinyl ketone 4a was added-to a THF solution of 2, the reaction mixture gradually changed from light brown to deep purple. After chromatographic purification, two types of δ-oxo selenothioic acid S-esters [6], 5a and 6a, were obtained in respective yields of 34% and 13% (entry 1). Since the Michael addition of lithium enethiolates of dithioic acid esters to ␣,␤-unsaturated ketones proceeds with high efficiency [7], a similar reaction using the lithium eneselenolate generated from ester 2 was attempted, but only a complex mixture was formed.…”

Section: Resultsmentioning

confidence: 99%

Reaction of an ammonium eneselenolate derived from a selenothioacetic acid S‐ester with electron‐deficient alkenes and alkynes

Murai

Kondo

Katō

2004

Heteroatom Chemistry

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Ammonium eneselenolate 2 derived from selenothioic acid S-ester 1 was reacted with electron-deficient alkenes 4 and alkynes 9. Ammonium eneselenolate 2 underwent Michael addition with 4 to give two types of Michael adducts, 5 and 6. Products 6 incorporated two molecules of 4. In contrast, the reaction of 2 with 9 took place at the selenium atom to give ␥ -oxo divinyl selenides 10 with high Z-stereoselectivity. During the further elaboration of the reactivity of the products derived from 2 and carbonyl compounds, unexpected reaction was found in the addition of vinylmagnesium bromide to Se-vinyl ester 3. The spectroscopic data supported the formation of the enol form 12 of ␤-oxo selenothioic acid Sester 13.

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Section: Resultsmentioning

confidence: 99%

Reaction of an ammonium eneselenolate derived from a selenothioacetic acid S‐ester with electron‐deficient alkenes and alkynes

Murai

Kondo

Katō

2004

Heteroatom Chemistry

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“…Although we also described the synthetic approach to tin−chalcogen double-bond compounds, Tbt(Tip)SnX (Tip = 2,4,6-triisopropylphenyl; X = S, Se), by dechalcogenation of 1,2,3,4,5-tetrachalcogenastannolanes and chalcogenation of the corresponding stannylene, they were found to be stable only in solution and dimerize in the solid state. With regard to three-membered ring compounds of heavier group 14 elements, a relatively large number of examples have been described 1 including those containing one chalcogen atom, but there is no precedent which contains two chalcogen atoms in the ring …”

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confidence: 99%

The First Kinetically Stabilized Stannaneselone and Diselenastannirane: Synthesis by Deselenation of a Tetraselenastannolane and Structures

1997

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“…Dithiiranes bearing CS 2 rings, disulfides incorporated into the smallest ring system, have long received fundamental curiosity as fascinating synthetic targets. The first synthesized derivative is an S ‐oxide, [9] and then its reactivity and other derivatives were successively reported [10] . On the other hand, a diselenirane and a ditellurirane remain unprecedented, even though the intermediary formation of a diselenirane was proposed [11] .…”

Section: Introductionmentioning

confidence: 99%

Main Group Analogs of Dichalcogeniranes

Saito,

Tokitoh,

Okazaki

2024

Eur J Inorg Chem

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This Mini Review highlights recent advances in the preparation of main group analogs of dichalcogeniranes. The three‐membered ring compounds are an intriguing class of compounds in terms of their strained structures and high reactivity. As for three‐membered rings composed of a carbon and two group 16 atoms, dioxiranes have long been utilized as oxidants, while some dithiiranes have been synthesized. In contrast, diselenirane and ditellurirane remain elusive. On the other hand, the chemistry of three‐membered rings consisting of a non‐carbon main group atom and two group 16 atoms has recently gained significant track. These emerging three‐membered ring compounds were characterized by X‐ray diffraction analysis on many occasions, revealing unique molecular structures with very long chalcogen−chalcogen single‐bond distances in some cases. A common reactivity is dechalcogenation reactions using phosphine reagents, which provide access to the corresponding double‐bonded compounds. This minireview covers recent advances in the synthesis of main group analogs of dioxirane, dithiirane, diselenirane, and even ditellurirane.

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First isolable dithiiranes: 3-(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-3-phenyldithiirane 1-oxides

Abstract: Ph3P (1.3 quiv) 4 * 6 + Ph,P=S c w 3 2 , r . 1 . 79%(6,44)

Cited by 48 publications

References 1 publication

Reaction of an ammonium eneselenolate derived from a selenothioacetic acid S‐ester with electron‐deficient alkenes and alkynes

Reaction of an ammonium eneselenolate derived from a selenothioacetic acid S‐ester with electron‐deficient alkenes and alkynes

The First Kinetically Stabilized Stannaneselone and Diselenastannirane: Synthesis by Deselenation of a Tetraselenastannolane and Structures

Main Group Analogs of Dichalcogeniranes

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