Thermolysis of thiete 1,1-dioxide and related species

King, Jimmie; Mayo, P. De; McIntosh, C. L.; Piers, K.; Smith, David J.

doi:10.1139/v70-619

Cited by 99 publications

(14 citation statements)

References 9 publications

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“…Sultine 9 is also produced on thermolysis of 1, as described in the accompanying paper (I), and its formation and n.m.r. spectrum were of interest in connection with the formation of sultines by thermal rearrangement of thiete 1,ldioxide and derivatives (10). The anisotropy of the sulfinyl group is such that in a group of these sultines (10) the chemical shifts of the two methylene protons were found to differ by as much as 0.67 p.p.m.…”

Section: Resultsmentioning

confidence: 99%

Chlorination of Heterocyclic and Acyclic Sulfonhydrazones

King¹,

Hawson²,

Huston³

et al. 1971

Can. J. Chem.

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Chlorination of 2H-1,2,3-benzothiadiazine 1,1-dioxide(1) in wet methylene chloride gives o-formylbenzenesulfonyl chloride (4), but in dry methylene chloride at 0° yields the chlorosultine 3-chloro-3H-2,1-benzoxathiole 1-oxide (2); the latter is readily hydrolyzed to the "pseudo-acid" 3H-2,1-benzoxathiol-3-ol 1-oxide (3) which on further chlorination forms 4. In 1,2-dichloroethane at −20° chlorination of 1 gave the "coupled product" 14, whereas in dimethylformamide at room temperature the cyclic acyl chloride hydrazone 4-chloro-2H-1,2,3-benzothiadiazine was isolated in poor yield. The acyl chloride hydrazones (16) were the products obtained following chlorination of some representative aromatic acyclic tosylhydrazones (15). 3H-2,3,4-Benzothiadiazepine2,2-dioxide (19), a previously unknown heterocyclic system, was synthesized in two steps from 1,3-dihydrobenzo[c]thiophene (17). Chlorinolysis of 19 gave o-chloromethylbenzal chloride (21). These reactions are believed to involve formation of the α-chloroazo compound (e.g. 22) as the first step. The formation of 2 from 1 is discussed in terms of three possible routes, two which involve the sulfene 23.

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Section: Resultsmentioning

confidence: 99%

Chlorination of Heterocyclic and Acyclic Sulfonhydrazones

King¹,

Hawson²,

Huston³

et al. 1971

Can. J. Chem.

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“…Preparative t.1.c. of the remaining solid (CHCI,) yielded 2.5% of the cyclopentadienone dimer (2) Thermolysis of2,5-Diphenyl-p-benzoquinone (4) 2,5-Diphenyl-p-benzoquinone(550 mg; Eastman Organic) was passed through the oven at 1180", with 100 p of nitrogen gas as carrier, over a period of 6 h. The solid left on the cold finger after pressurization and removal of liquid nitrogen was separated by preparative t.1.c. to yield l-phenylnaphthalene (5) (8%), 2-phenylnaphthalene (6) (873, benzo-[1,2-b:4,5-b'lbisbenzofuran (7) (6%), and 6% starting material.…”

Section: Methodsmentioning

confidence: 99%

“…lb of ref. 4. A platinum-rhodium resistor heater coil was used to reach the higher temperatures (above 1200°), but the coils had comparatively short life-times and could not be used at temperatures higher than 1350 "C. At 13 lo0, the maximum temperature at which the oven could be maintained for time enough to carry out 4 5 thermolyses before burning out the coil, p-benzoquinone gave the dimer of cyclopentadienone in 2.5% yield.…”

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confidence: 99%

Flash Thermolysis: Quinones

Champlain¹,

Mayo²

1972

Can. J. Chem.

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“…In order to produce larger amounts of material, ( I ) , (3), (5), and (7) were pyrolyzed in a highvacuum now apparatus. Compounds (I), (3), and ( 5 ) afforded ( 2 ) , ( 4 ) , and ( 6 ) in yields of 29 %, 42 %, and 41 %, respectively. The major product obtained on pyrolysis of (7) + 0 was found, by comparison of its UV, IR, and mass spectrum and of its gas chromatogram with those of authentic materito be indeno[2,1-a]indene (9).…”

Section: Elimination Of Co From Cyclic Carbonyl Compounds By Flow Pyrmentioning

confidence: 99%