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Thermal rearrangement of xanthates to dithiolcarbonates-II. Mechanism study

✍ Scribed by Tanezo Taguchi; Yuichi Kawazoe; Michiko Nakao

Publisher
Elsevier Science
Year
1963
Tongue
French
Weight
223 KB
Volume
4
Category
Article
ISSN
0040-4039

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✦ Synopsis

IH the first paper* of this series, the unusual cese of the Chugeer rea&ioll that pyrolysis causes rearrangement of zsnthstes to dithiolcsrbonstes with retention of configuration was reported. The perticipztim of nelghbm Srnqwsa founl. ueCessaryforthe reerrsnge mezt, because the resrrsqement tookplece only onthetreat~nt of compounds holdingauanchimerlo group adjacent to the zsnthste group, suCh seB4imethyle&~~U@ S-met@1 zsnthste (I). There sre three possible pathways for the reerrenge mslltof1; (a) through a SMi-type mechauism to &ford III, (b) throu& 1,2-shift to afford IV end (c) through both together to afford III srzi IV. I'yrolyeis of '"H3'K 85yJH3 44&i-A -&AH-__* (c&j)# y(cH3)2 -CH<H-+/or T-CH-O* ,S s 0 F III =3 DL-disstereomers of l-phenyl-2-di.zathyl&opropylS-~thylxsuthste (V) yielded the corresponding dithiolcsrbonetesZ without any shift of group, ' StudiesinStereochemistry XXX.

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