79164-15-1

Upstream product

• 68480-28-4 formiate de methyl-3 butene-2 ol-1 
• 556-82-1 3-methyl-2-buten-1-ol 
• 65755-82-0 (prenyloxy)acetophenone 
• 101-48-4 phenylacetaldehyde dimethyl acetal 
• 79164-19-5 3,3-dimethylallyl 2-phenylvinyl ether 
• 99309-29-2 (3-methyl-but-2-enyloxy)acetic acid 
• 170502-95-1 2-(3-methyl-but-2-enyloxy)-N-methoxy-N-methyl-acetamide 

Downstream Products

• 349465-30-1 (8aS)-3(Z)-(3,3-dimethyl-2-phenyl-4-pentenylidene)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant academic research and scientific papers

Non-carbonyl-stabilized metallocarbenoids in synthesis: The development of a tandem rhodium-catalyzed bamford-stevens/thermal aliphatic claisen rearrangement sequence

A tandem rhodium-catalyzed Bamford-Stevens/Claisen rearrangement is presented. The tandem reaction uses Eschenmoser hydrazones for the in situ generation of non-carbonyl-stabilized diazo alkanes, which are presumably intercepted by Rh(II) catalysts to induce a 1,2-hydride migration. This sequence provides high levels of stereocontrol for the generation of simple acyclic (Z)-enol ethers. These enol ethers undergo either thermal or Lewis acid accelerated Claisen rearrangements to provide products of high diastereopurity. Also presented are cascade reactions, wherein a third chemical step occurs after the initial tandem sequence (i.e., Bamford-Stevens/Claisen/ene and Bamford-Stevens/Claisen/Cope). Copyright

Intermolecular and intramolecular Diels-Alder cycloadditions of 3-ylidenepiperazine-2,5-diones and 5-acyloxy-2(1H)-pyrazinones

The 3-ylidenepiperazine-2,5-diones 16 and 39 and 5-acyloxy-2(1H)-pyrazinones 17 can serve as starting materials for the Diels-Alder reactions of alkenes and alkynes to the piperazine ring, under acidic conditions or in the presence of acetyl chloride, to afford tricyclic piperazine-2,5-diones 19, 20, 23-25, 27, 44, and 45. Intramolecular cycloadditions occur if 3-ylidenepiperazine-2,5-diones 30 and 32 are used as the starting materials. This procedure is a convenient path to bridged bicyclo-[2.2.2]diazaoctane ring systems such as 31 and 33, the former being found in biologically active secondary mold metabolites, such as VM55599 (1) or brevianamide A (5), which have been isolated from various fungi. The synthesis of the indole compound 31 provided evidence for the proposed biochemical pathway with a Diels-Alder reaction as key step. Quantum chemical calculations have revealed that piperazinones with a cationic azadiene moiety are the most reactive species in Diels-Alder cycloadditions.

PREPARATION OF ALLYL VINYL ETHERS BY WITTIG REACTION OF ALLYL FORMATES

Substituted allyl vinyl ethers are obtainable by the reaction of allyl formates with Wittig reagents.Reactivity of some of the produced allyl vinyl ethers was also examined.