New radical allylation reaction

Journal of the American Chemical Society

Volumn 118, Issue 5, 1996, Pages 1209-1210

  Quiclet Sire, Béatrice ^a   Zard, Samir Z ^a,b  

^a CNRS   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030002988     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9522443     Document Type: Article

References (52)

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40. Thermolysis of alkyl or aryl allyl sulfones at 300 °C was found to lead to rearrangement with extrusion of sulfur dioxide to give compounds of type 3 by what was presumed to be a pericyclic mechanism: Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3609-3610. Whitham and Phillips (ref 6a) report observing a small amount of a side product in one of their experiments where desulfonative allylation appears to have occurred.
41. A typical experimental procedure is as follows: A solution of alkyl allyl sulfone 1a-d (1 mmol) and allyl tolyl sulfone 5 (3-6 mmol) in a degassed mixture of cyclohexane (3 mL) and toluene (1 mL) was heated under reflux in the presence of AIBN (10-15%, added portionwise over the course of the reaction). For examples 3a and 3b, chlorobenzene (3 mL) was used with di-tert-butyl peroxide (one drop) as initiator. The reaction, monitored by TLC, took 2-8 h, The solvents were evaporated under reduced pressure, and the residue was chromatographed on a silica gel column to afford the desired allyl derivatives 3a-d. In the case of addition to an external electrophilic olefin 7a-c (1 mmol), the relay sulfone 5 was omitted and an excess of alkyl allyl sulfone 1e-k (6 mmol) was added. Again a mixture of cyclohexane and toluene was used for most examples, except for 8i. where 1,2-dichloroethane proved a better solvent, and 8c,f, where the reaction was performed in chlorobenzene (di-tert-butyl peroxide as initiator).
42. It is interesting to note that addition of p-tolylsulfonyl radicals to diallyl sulfone at room temperature is reported to lead mostly to a cyclic sulfone. This gives an idea of the rate of β-elimination of a sulfonyl radical, which must be somewhat slower, at least at room temperature, than a 5-exo-dig cyclization in this case: Serra, A. C.; da Silva Corrêa, C. M. M.; Vieira. M. A. M. S. A.; Gomes, M. A. Tetrahedron 1990, 46, 3061-3070.
43. We have found that S-allyl or S-propargyl xanthates are synthetically useful sources of allyl and propargyl radicals, which can be trapped in an inter- or intramolecular fashion: (a) Mestre, F.; Tailhan, C.; Zard, S. Z. Heterocycles 1989, 28, 171-174.
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