129454-82-6

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 13159-16-5 (E)-5-phenyl-4-penten-1-ol 
• 54911-85-2 4-tetrahydropyranyloxybutanal 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 591-50-4 iodobenzene 
• 159646-45-4 2-(5-bromopent-4-ynyloxy)tetrahydro-2H-pyran 
• 63082-55-3 diethyl (E)-cinnamyl malonate 
• 51326-51-3 4-(tetrahydropyran-2-yloxy)butan-1-ol 
• 3708-36-9 trans-cinnamylmalonic acid 
• 28525-69-1 (4E)-5-phenyl-4-pentenoic acid 

Downstream Products

• 36884-75-0 (E)-5-phenylpent-4-enal 
• 92609-30-8 2-(2,2-dichloro-t-3-phenyl-r-1-cyclopropyl)-1-propanol-tetrahydro-2-pyranyl ether 
• 13159-16-5 (E)-5-phenyl-4-penten-1-ol 
• 92609-35-3 t-3-t-butoxy-c-2-(2-hydroxypropyl)-c-3-phenyl-r-1-cyclopropanecarboxylic acid lactone 
• 92609-32-0 1-chloro-c-2-(2-hydroxypropyl)-t-3-phenyl-r-1-cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Stille reactions catalytic in tin: A "Sn-F" route for intermolecular and intramolecular couplings

(Chemical Equation Presented) Polymethylhydrosiloxane (PMHS) made hypercoordinate by KF(aq) allows Me3SnH to be recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Starting with a variety of alkynes, in situ vinyltin formation is followed by Stille reaction with aryl, styryl, benzyl, or vinyl electrophiles present in the reaction mixture. Both inter- and intramolecular versions of the process are possible with tin loads of approximately 6 mol %. Regeneration of the organotin hydride is believed to proceed through a Me3SnF intermediate. Given the aggregated nature of organotin fluorides and the ability to use these organotins in substoichiometric quantities, the hazards and purification problems associated with the removal of organotin wastes from reaction mixtures are minimized.

Stille couplings catalytic in tin: The "Sn-O" approach

A one-pot tandem Pd-catalyzed hydrostannylation/Stille coupling protocol for the stereoselective generation of vinyltins and their subsequent union, employing only catalytic amounts of tin, is described. By recycling the organotin halide Stille byproduct back to organotin hydride, a hydrostannylation/cross-coupling sequence can be carried out with catalytic amounts of tin. Such a process is most effective with Me3SnCl serving as the tin source. This protocol allows a 94% reduction of the tin requirement, while maintaining good yields (up to 90%) for a variety of Stille products. Furthermore, since one cycle requires the tin to undergo at least four transformations, each moiety of trialkyltin is experiencing a minimum of 60 reactions over the course of the hydrostannylation/Stille, sequence.

INTRAMOLECULAR REACTIONS OF ALLYLOXY RADICALS

Allyloxy radicals formed by epoxide cleavage, have cyclised onto appropriately positioned alkenes to form tetrahydrofurans, and the diastereoselectivity of the cyclisation has been studied.The reaction was used to synthesise lilac alcohols which were then used to confirm the stereochemistry of such cyclisations.

REACTIVITY OF 1-CYCLOPROPENE-1-LACTONES DEPENDENT ON THE SUSBSTITUTION DEGREE

Reaction of the α-chloro lactone 10 with KOtBu gives the butoxy lactones 21 and 22; the seven membered derivative 11 leads 23 as the only isolable product.Formation of the α-substitution product 21 as well as the enhanced instability of the intermediates 12 and 13 in comparison to their methyl substituted homologues 5 and 6 show the kinetical stabilization by a methyl group at C-2.Products derived from a cyclopropeno lactone of type A could not be detected.