Lewis acid catalysed M-ene, H-ene, and cycloaddition reactions of allylic stannanes and silanes with methyl propiolate

The products of the reaction of methyl propiolate with cyclohexene and some allyl and cyclohex-2-enyl silanes and stannanes (H-ene and M-ene adducts, and [2+2] and [3+2] cycloadducts) have been determined, and rationlised in terms of the probable reaction mechanism. The allylstannanes show only the...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 553; no. 1; pp. 67 - 72
Main Authors Dang, Hai-Shan, Davies, Alwyn G.
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier B.V 25.02.1998
Elsevier
Subjects
Allylsilanes
Allylstannanes
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Ene reaction
Metalloene reaction
Physical Sciences
Sakurai reaction
Science & Technology
Sakurai reaction
Ene reaction
Metalloene reaction
Allylstannanes
Allylsilanes
ene reaction
metalloene reaction
STANNYLATED CHOLESTENES
allylsilanes
3-BUTYN-2-ONE
ALLYLTRIMETHYLSILANE
allylstannanes
REARRANGEMENT
TRIMETHYLSILYLCYCLOPENTANE ANNULATION
3+2 CYCLOADDITIONS
SINGLET OXYGEN
CONJUGATE ADDITION
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Summary:The products of the reaction of methyl propiolate with cyclohexene and some allyl and cyclohex-2-enyl silanes and stannanes (H-ene and M-ene adducts, and [2+2] and [3+2] cycloadducts) have been determined, and rationlised in terms of the probable reaction mechanism. The allylstannanes show only the M-ene reactions to give a mixture of the E- and Z-adducts, and it has been confirmed that the reaction of allylsilanes can give both the [2+2] (cyclobutene) and [3+2] (cyclopentene) cycloadducts, which has been a matter of some dispute.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(97)00246-5