a-Bromovinyl Methyl Sulfone

[35495-31-9]  · C3H5BrO2S  · a-Bromovinyl Methyl Sulfone  · (MW 185.05)

(dienophile equivalent to allene in cycloaddition reactions via Ramberg-Bäcklund reaction of the adducts;1 gives aziridines with primary amines in DMSO2)

Physical Data: bp 63-64 °C/0.4 mmHg.

Solubility: sol common organic solvents.

Form Supplied in: colorless liquid; not commercially available.

Preparative Method: prepared by bromination-dehydrobromination of methyl vinyl sulfone in 80% yield.1

The reaction of a-bromovinyl methyl sulfone with cyclopentadiene affords a mixture of the expected cycloadducts which, upon treatment with Sodium Methoxide in DMSO, give 5-methylene-2-norbornene via the Ramberg-Bäcklund rearrangement in over 90% yield. Using 2N Sodium Hydroxide as the base, the adducts give, besides the expected 5-methylene-2-norbornene, 37-59% yield of the rearranged adduct (eq 1).1 The latter product arises from a radical rearrangement.

The action of Dimethyl Sulfoxide and a primary amine on a-bromovinyl methyl sulfone gives aziridines (eq 2).2

1. Philips, J. C.; Oku, M. JACS 1972, 94, 1012.
2. Gaillot, J.-M.; Gelas-Mialhe, Y.; Vessiere, R. CJC 1979, 57, 1958.

Ottorino De Lucchi

Università di Venezia, Italy

Giovanna Delogu

Istituto CNR, IPATCAPA, Sassari, Italy

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