- Thermal Reactions of 2-Alkyl (or Aryl)-1-benzoyl-3,4-dihydro-1H-2-thionianaphthalen-1-ides with Compounds possessing an Acidic Hydrogen
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Thermal reactions of 2-alkyl-1-benzoyl-3,4-dihydro-1H-2-thionianaphthalen-1-ides (1a-d) in ethanol afforded alkyl o-vinylbenzyl sulphides (2a-d) along with ethyl benzoate, whereas that of the 2-phenyl congener (1e)-gave o-(ethoxymethyl)phenethyl phenyl sulphide (3) together with the sulphide (2e).The ylides (1a and e) reacted with boiling water to afford the benzoates (9a and e).Reactions of the ylides (1a-e) with carboxylic acids and thiols gave the ring-opening products (11)-(17), cleaving the C(1)-S bond.Reactions of the ylide (1a) with succinimide or phthalimide yielded the ring-expansion product 2-phenyl-4,5-dihydro-3,5-benzoxathionine (19).In the reaction of the ylide (1a) with phenol, the product proportions changed with amounts of phenol.When 2 equiv. of phenol were used, the oxathionine (19) was obtained.However, the ring-opening products (22) and (23) were formed by using 10 or 100 equiv. of phenol.These reactions are initiated by protonation on the ylidic carbanion to form the sulphonium salt (5).The conjugate base formed concurrently attacks a different reaction site, viz. a carbonyl carbon, C(1), or a methyl proton of the sulphonium salt (5), depending on its character.
- Kataoka, Tadashi,Tomoto, Akihiko,Shimizu, Hiroshi,Imai, Eiji,Hori, Mikio
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p. 515 - 521
(2007/10/02)
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- Syntheses and Thermal Reactions of Cyclic Sulphenium Ylides: 2-Alkyl(or aryl)-1-benzoyl-1H-thianaphthalen-2-ium-1-ides and 2-Alkyl(or aryl)-1-benzoyl-3,4-dihydro-1H-2-thianaphthalen-2-ium-1-ides
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Pummerer cyclization of phenacyl phenethyl sulphoxide (5) was carried out using trifluoroacetic anhydride to give 1-benzoyl-3,4-dihydro-1H-2-thianaphthalene (6) in a good yield.Alkylation (or arylation) of 1-benzoyl-1H-2-thianaphthalene (1) and the 3,4-di
- Kataoka, Tadashi,Tomoto, Akihiko,Shimizu, Hiroshi,Hori, Mikio
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p. 2913 - 2920
(2007/10/02)
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- SYNTHESIS AND THERMAL REACTIONS OF 2-ALKYL(OR ARYL)-1-BENZOYL-3,4-DIHYDRO-2-THIANAPHTHALENES
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1-Benzoyl-2-methyl-3,4-dihydro-2-thianaphthalene (4a) underwent novel intermolecular 1,4-rearrangement in refluxing toluene to give an enol ether 5a, while rearrangement of 2-phenyl derivative 4e proceeded intramolecularly in refluxing xylene to afford a 1,4-rearranged enol ether 5b.On the other hand, ylides 4a-e were refluxed in alcohols to afford some ring-opened products 10-12.
- Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Tomoto, Akihiko
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p. 3629 - 3632
(2007/10/02)
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- ELECTROPHILIC AROMATIC SUBSTITUTION BY PUMMERER REACTION OF α-SULFINYLACETATE
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Treatment of a mixture of aromatic compound and ethyl α-(methylsulfinyl)acetate (5) with p-toluenesulfonic acid under continuous removal of separated water brought about an intermolecular aromatic substitution to give ethyl α-(methylthio)arylacetate (6).S
- Tamura, Y.,Choi, H.-D.,Shindo, H.,Uenishi, J.,Ishibashi, H.
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