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A Study on the Reaction of Lithiated Allyl Systems with CO2, Isocyanates and Isothiocyanates

✍ Scribed by Michaela Piffl; Jennie Weston; Ernst Anders

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 422 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200008)2000:16<2851::aid-ejoc2851>3.0.co;2-x

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✦ Synopsis

The regioselectivity of the reaction of 1-(thiophenyl)-(Li-6), 1-(phenylsulfinyl)-(Li-12), 1-(phenylsulfonyl)-(Li-15) and 1-(diethoxyphosphoryl)allyllithium (Li-18) with CO 2 , PhNCO and PhNCS is investigated. Carboxylation of the allyl sulfide 6 and the allyl sulfoxide 12 proceeds with low regioselectivity. On the other hand, an exclusive γ-selectivity is achieved for reactions of CO 2 with Li-15 and Li-18. Both carboxylations are reversible and can be directed to give α-products by using low temperature workup (0 °C). In contrast to

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