80253-06-1Relevant academic research and scientific papers
General procedure for the synthesis of ortho-vinylbenzyl-substituted amines, ethers, and sulfides
Shcheglova,Kolesnik,Ashirov
, p. 1329 - 1334 (2013/11/06)
A convenient procedure has been proposed for the synthesis ortho-vinylbenzyl-substituted ethers, amines, and sulfides via reaction of o-(2-bromoethyl)benzyl bromide with various nucleophiles.
A New Method for Radical Generation: Reductive C-Se or C-S Bond Cleavage of Cyclic Onium Salts
Kataoka, Tadashi,Tsutsumi, Kazuhiro,Kano, Kenji,Mori, Kazuya,Miyake, Miho,et al.
, p. 3017 - 3025 (2007/10/02)
2-Methyl-3,4-dihydro-1H-2-benzoselenopyranium salt (1) was reduced by some metallic reagents or magnesium metal via the single-electron transfer (SET) process to give 2--toluene (2).Magnesium metal was a good SET reducing agent.Some other selenonium or sulphonium salts (7), (14), (22), (27) and (32) were similarly reduced by magnesium.Particularly, sonication accelerated the reductions. ε-Eneselenonium salt (43) was treated with activated magnesium to give a cyclised pyrrolidine derivative (44).
Thermal Reactions of 2-Alkyl (or Aryl)-1-benzoyl-3,4-dihydro-1H-2-thionianaphthalen-1-ides with Compounds possessing an Acidic Hydrogen
Kataoka, Tadashi,Tomoto, Akihiko,Shimizu, Hiroshi,Imai, Eiji,Hori, Mikio
, p. 515 - 521 (2007/10/02)
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.
SYNTHESIS AND THERMAL REACTIONS OF 2-ALKYL(OR ARYL)-1-BENZOYL-3,4-DIHYDRO-2-THIANAPHTHALENES
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Tomoto, Akihiko
, p. 3629 - 3632 (2007/10/02)
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.
