119760-32-6

Basic information

• Product Name: (1S,2S,10bS)-1,2-Bis-benzenesulfonyl-1,5,6,10b-tetrahydro-2H-isoxazolo[3,2-a]isoquinoline
• CAS NO: 119760-32-6
• Molecular Weight: 455.555
• Mol File: 119760-32-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2S,10bS)-1,2-Bis-benzenesulfonyl-1,5,6,10b-tetrahydro-2H-isoxazolo[3,2-a]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,10bS)-1,2-Bis-benzenesulfonyl-1,5,6,10b-tetrahydro-2H-isoxazolo[3,2-a]isoquinoline(119760-32-6)
• EPA Substance Registry System: (1S,2S,10bS)-1,2-Bis-benzenesulfonyl-1,5,6,10b-tetrahydro-2H-isoxazolo[3,2-a]isoquinoline(119760-32-6)

Safety Data

• Hazardous Substances Data: 119760-32-6(Hazardous Substances Data)

Upstream product

• 24423-87-8 3,4-dihydro-isoquinoline 2-oxide 
• 963-15-5 (Z)-1,2-bis(phenylsulfonyl)ethene 

Relevant articles and documents

STERIC EFFECTS VS SECONDARY ORBITAL INTERACTIONS IN NITRONE CYCLOADDITIONS. STERIC EFFECTS IN CYCLOREVERSIONS OF ISOXAZOLIDINES.

3,4-Dihydroisoquinoline-N-oxide 1 reacted readily with both acyclic (Z)- and (E)-disubstituted alkenes bearing electron-attracting substituents (methoxycarbonyl, cyano, phenylsulphonyl and benzoyl groups) and with cyclic derivatives (e.g.) maleimides) to give mixtures of the two possible diastereoisomers.Similar amounts of endo- and exo-adducts were formed in the reactions of (Z)-cyano, methoxycarbonyl and benzoyl derivatives whereas exo-addition clearly won over its endo-counterpart in the case of (Z)-(phenylsulphonyl) and cyclic derivatives.High exo-selectivity was also observed in the sluggish reactions of 1 with electron-rich alkenes .Our results, which revise previous literature data, clearly show that an "endo-rule" does not hold for the reactions of 1 with (Z)-1,2-disubstituted alkenes.We conclude that in these reactions repulsive steric interactions either counteract efficiently or clearly win over stabilizing secondary orbital overlaps in controlling endo/exo-selectivity.These reactions were found reversible under mild conditions so that relative formation rates of related pairs of (Z)- and (E)-dipolarophiles in cycloreversion processes of isoxazolidines could be determined; as a rule (E)-alkenes are extruded faster than (Z)-isomers.These results provide unambiguous experimental evidence that increase in steric compression between the substituents in (Z)-alkenes, on their way toward transition state, is not a major factor in determining their lower reactivity with respect to (E)-isomers in 1,3-dipolar cycloadditions.