Synthesis and thermolysis of novel spiroselenuranes bearing two oxaselenetane rings: double oxirane formation reactions from 1,5-dioxa-4λ4-selenaspiro[3.3]heptanes

Ohno, F.; Kawashima, Takayuki; Okazaki, Renji

doi:10.1039/b009789f

Cited by 24 publications

(6 citation statements)

References 5 publications

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“…15 The addition of a catalytic amount of CuI also had a drastic effect on the reaction of 1 with arylmagnesium bromides. The reaction in the presence of CuI catalyst rapidly proceeds at low temperature leading to the formation of aryl derivatives 12, 16 13a and 13b (Scheme 9).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Polyfluorinated Tertiary Alcohols Using Ring Opening Reactions of 2,2-Bis(trifluoromethyl)oxirane

Петров¹

2002

Synthesis

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This paper describes new reactions of 2,2-bis(trifluoromethyl)oxirane (1). Ring opening of 1 by oxygen, nitrogen, sulfur or carbon nucleophiles (Nu -) proceeds regioselectively, with exclusive formation of tertiary alcohols: NuCH 2 C(CF 3 ) 2 OH. The reaction of 1 with strong acids (HX) is also regioselective and proceeds under mild conditions leading to the formation of XCH 2 C(CF 3 ) 2 OH (X = FSO 2 O, CF 3 SO 2 O, Cl, I). The addition of acetic acid to 1, however, requires an elevated temperature and TaF 5 a catalyst. Highly selective reactions of 1 with nucleophilic or electrophilic reagents provide a simple and general route to materials containing CH 2 C(CF 3 ) 2 OH group.

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Section: Methodsmentioning

confidence: 99%

“…Compounds 2, 10 2a, 11 6, 8 12, 16 16a, 20 and 17a 22 were identified by comparison of boiling points or NMR data with reported values.…”

Section: Scheme 15mentioning

confidence: 99%

Synthesis of Polyfluorinated Tertiary Alcohols Using Ring Opening Reactions of 2,2-Bis(trifluoromethyl)oxirane

Петров¹

2002

Synthesis

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“…63,64 Recently, spirocyclic Se and Te systems 17, containing four-membered rings were investigated. 66,67 In these cases a considerable distortion of the trigonal bipyramidal struc- ture was found; the OÀ ÀSeÀ ÀO and OÀ ÀTeÀ ÀO angles were as low as 155.38 and 148.18, respectively (Scheme 9).…”

Section: X-ray Crystallographymentioning

confidence: 97%

Recent advances in spirochalcogenurane stereochemistry—A mini review

Allenmark¹

2008

Chirality

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“…5 Furthermore, we have also synthesized spiro compounds bearing two oxetane rings, namely, spirobi[1,2-oxaphosphetane], 6 , spirobi[1,2-oxasiletanide], 7 and spirobi[1,2-oxaselenetane]. 8 In the last account, 9 we reported four-membered heterocycles containing highly coordinated group 16 elements. Here, we wish to summarize our results concerning four-membered heterocycles containing highly coordinated sulfur atom as well as some our previous results.…”

Section: Introductionmentioning

confidence: 96%

Chemistry of Four-Membered Ring Compounds Containing a Hypervalent Sulfur Atom and a Heteroatom at the Neighbor Positions

Kawashima

2011

Phosphorus, Sulfur, and Silicon and the Related Elements

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Title compounds containing tetracoordinated and pentacoordinated sulfur together with oxygen, nitrogen, or sulfur were successfully synthesized as stable compounds. They contain the Martin ligand, which is well known to be able to stabilize such highly coordinated main group compounds. X-ray crystallographic analyses revealed that they have distorted trigonal bipyramidal (TBP) or pseudo-TBP structures. In marked contrast to group 13-15 element analogues, which afford the corresponding alkenes upon heating, thermolyses of compounds bearing an oxygen or nitrogen atom gave the corresponding oxiranes or aziridine, suggesting the possibility that these compounds are intermediates of the Corey-Chaykovsky reaction of sulfur ylides with carbonyl compounds or imines. Thermolysis of 1λ 4 ,2-dithietanes also gave the corresponding thiiranes. The stereochemistry (retention of configuration) of formation of these three-membered ring compounds is also described.

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Synthesis and thermolysis of novel spiroselenuranes bearing two oxaselenetane rings: double oxirane formation reactions from 1,5-dioxa-4λ4-selenaspiro[3.3]heptanes

Cited by 24 publications

References 5 publications

Synthesis of Polyfluorinated Tertiary Alcohols Using Ring Opening Reactions of 2,2-Bis(trifluoromethyl)oxirane

Synthesis of Polyfluorinated Tertiary Alcohols Using Ring Opening Reactions of 2,2-Bis(trifluoromethyl)oxirane

Recent advances in spirochalcogenurane stereochemistry—A mini review

Chemistry of Four-Membered Ring Compounds Containing a Hypervalent Sulfur Atom and a Heteroatom at the Neighbor Positions

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