7228-52-6Relevant academic research and scientific papers
REACTION OF CHLOROSULFONYL ISOCYANATE WITH 1,2-DIOLS: REARRANGEMENT AND FORMATION OF CARBONATES
Joseph, Sajan P.,Dhar, D. N.
, p. 2295 - 2302 (2007/10/02)
1,2-Diols, 1a-e, upon reaction with chlorosulfonyl isocyanate (CSI) gave the ketones, 3a-e.Under similar experimental conditions, 1,2-diols, 1f-k, gave carbonyl compounds, 3f-k, carbonates, 6f-k, carboxamides, 7h,i, and the epoxide, 5i.
Original Syntheses of Carbonyl Compounds and gem-Dihalocyclopropanes from β-Hydroxylalkylselenides
Krief,A.,Laboureur, J. L.,Dumont, W.
, p. 1549 - 1552 (2007/10/02)
β-hydroxyalkylselenides possessing two alkyl substituents on the carbon bearing the selenyl moiety react with dihalocarbenes generated from haloforms and thallous ethoxide or under phase transfer catalysis to produce ring enlarged ketones as the sole product in the first case, as the main product in the second.The reaction takes another course when the dihalocarbenes generated from haloforms and tBuOK or from trihalomethylphenylmercury are employed and leads inter alias to dihalocyclopropanes.
Reaction of p-Nitrobenzenesulfonyl Azide with Alkylidenecycloalkanes
McManus, Samuel P.,Ortiz, Margarita,Abramovitch, Rudolph A.
, p. 336 - 342 (2007/10/02)
The 1,3-dipolar addition of p-nitrobenzenesulfonyl azide (PNBSA) to alkylidenecycloalkanes 1-3 was studied, and the products of hydrolysis were isolated and identified.The products from 1 and 2 suggest that these alkenes react to give a single triazoline intermediate.The tetrasubstituted derivatives 3, however, give both possible reaction modes.The products initially derived from 3 were the two sulfonimides expected from ring expansion (4, R=R'=Me) and methyl migration (5).Upon hydrolysis, the respective ketones, 8 and 9, were obtained in excellent overall yields.The ring-expanded sulfonimides 4 (R=R'=Me, n=6-8) were found to be less reactive under hydrolytic conditions than their respective isomers 5.Thus, subjecting the PNBSA adducts to mild hydrolysis conditions allowed the isolation of pure 9 (n=6-8).Also, in two cases (i.e., n=7,8), the pure imides 4 (R=R'=Me, n=7,8) crystallized from the hydrolysis solutions.Dipolar cycloaddition of p-nitrobenzenesulfonyl azide to 2-isopropylidenebicycloheptane followed by acid hydrolysis gives endo-2-acetyl-exo-2-methylbicycloheptane (4.1 percent), exo-2-acetyl-endo-2-methylbicycloheptane (16.3 percent), 2,2-dimethylbicyclooctan-3-one (2.1 percent), and 3,3-dimethylbicyclooctan-2-one (36.8 percent), thus providing evidence that electronic factors are much more important than steric effects in controlling regioselectivity.
