Methyl methylsulfinylmethyl

SCH2COOEt) ° and with methyl methylsulfinylmethyl sulfide (MeSCH2SOMe) or methylthiomethyl p-tolyl sulfone (MeSCH2S02C6H4Me) (to give ArCH2-SMe), in each case with a Lewis acid catalyst. 

Methyl 2-methyllactate, m282 Methyl methyl-2-propenoate, m290 Methyl methylsulfinylmethyl sulfide, m315... 

Subsequent work on the deuteration and methylation of (methylsulfinylmethyl)benzene showed indeed that the proportions of the diastereomers produced depend on many factors. The 15 1 diastereomeric mixture of (rnethvlsulfinylmethyl-J) benzene from the deuteration with re-tention/methylation with inversion of (methylsulfinylmethyl)benzenc result45 was obtained in THK with methyllithium prepared from chloromethane (low content of lithium salts). When the methyllithium w as prepared from bromomethane (one equivalent of lithium bromide is present in the mixture), the ratio was reduced to 3 151. The same effect was produced by addition of one equivalent of lithium bromide to the reaction mixture prior to the addition of methyllithium prepared from chloromethane. Excess of lithium bromide reverses the ratio to 0.45 1. 

The condensation of DAMN with 1,2-diimino-l, 2-dimethoxyethane (70) gives 2-amino-5,6-dicyano-3-methoxypyrazine (71) (385), but as in the condensation of DAMN with DISN the control of acid concentration is critical. The condensation of DAMN with chloroacetone or pyruvaldehyde has been shown to give 23-dicyano-5-methylpyrazine (385) and DAMN with methylsulfinylmethyl phenyl ketone refluxed in ethanol gave 23-dicyano-5-phenylpyrazine (386a). A, 7V -Dichlorodi-iminosuccinonitrile (a2DISN) (72) reacts with some olefins to give pyrazines. Thus with styrene (73, R = Ph, R = H) in benzene it gave 23-dicyano-5-phenyl-pyrazine (74, R = Ph, R = H). Similar reactions were observed with /J-methyl-styrene and 23-dihydropyran (387). 

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