13261-70-6

Upstream product

• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 478072-06-9 2-allylbenzhydrazide 
• 139373-30-1 Trifluoro-methanesulfonate(2-methoxycarbonyl-1-oxo-indan-2-ylmethyl)-phenyl-trimethylsilanylmethyl-sulfonium; 
• 59838-69-6 1-(2-methylphenyl)-2-propyn-1-one 
• 201230-82-2 carbon monoxide 
• 24850-33-7 allyltributylstanane 
• 109586-43-8 o-(2-propenyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 17496-14-9 2,3-dihydro-2-methyl-1H-inden-1-one 
• 89506-40-1 2-(2-oxo-2-phenylethyl)-2,3-dihydro-1H-inden-1-one 
• 21725-92-8 3'-phenyl-4'H-spiro[indan-2,5'-isoxazol]-1-one 

Relevant academic research and scientific papers

Acyl hydrazines as precursors to acyl radicals

The use of acyl hydrazines (hydrazides) as precursors for the stoichiometric generation of acyl radicals is explored. Two classes of substrates are examined: unsubstituted acyl hydrazines and acyl hydrazines substituted with a leaving group (2-nitrobenzenesulfonyl or 'nosyl'). Both types are successfully converted to acyl radicals, and are then trapped by nitroxide radicals to give acyloxyamine products. Cyclization reactions are demonstrated for both classes of substrates. A low temperature modification of the McFayden-Stevens reaction is also developed.

A New Fragmentation Reaction of γ-Oxosulfonium Methylides

Reactions of sulfonium methylides attached to a 5- or 6-membered cycloalkanone undergo the ring-fission as a major reaction course to give α-methylene-ω-(phenylthio)carboxylates, whereas sulfonium methylides attached to a larger ring give α-methylenecycloalkanones predominantly.Reactions of the acyclic compounds are also examined.

THE FLOW THERMOLYSES OF 1-ISOBUTENYL ALKYNYL- AND 2-METHYLPHENYL ALKYNYL KETONES. SYNTHESIS OF METHYLENOMYCIN B

The gas flow thermolyses of 1-isobutenyl alkynyl and 2-methylphenyl alkynyl ketones were found to lead to phenols and to cyclopentenones.The results are explained by a 5-ring carbene process (the known α-alkynone cyclization) and a 6-ring as well as a 5-ring addition process.The latter two (novel) processes are thought to be intramolecular "C-H to CC additions" in two directions.The 5-ring addition process was used in a short (but low yield) synthesis of methylenomycin B.

The Gas-Flow Thermolysis of 1-Isobutenyl Alkynyl and 2-Methylphenyl Alkynyl Ketones. Synthesis of Methylenomycin B

The gas-flow thermolysis of 1-isobutenyl alkynyl or 2-methyphenyl alkynyl ketones were found to lead to phenols and cyclopentenones or to naphthols and indanones, respectively.These conversions involve two cyclization processes so far unknown with α-alkynones; they are interpreted as intramolecular additions of an allylic or a benzylic C,H bond to a triple bond which may occur in two directions.In addition, the cyclopentenones formed by the α-alkynone cyclization, a known carbene process yielding 5-rings, were also found.The available evidence ruled out a carbene process yielding 6-rings.The addition process yielding 5-rings was applied to a short (but low yield) synthesis of methylenomycin B.