Hello all
I thought it would be cool if we can make 2CT's from vanillin, so I searched the hive and the only thing I get was conversion of the 4-OH of vanillin with P2S5 in a post of dormouse. The discussion said that the aldehyde would be converted too and that seem bad to me.
I went to my local university and do a search for thiovanillin: I got this ref:
New key compounds in cyclotriveratrylene chemistry. Synthesis, optical resolution, absolute configuration and circular dichroism of C3-cyclotriveratrylenes with sulfur substituents. Garcia, Chantal; Andraud, Chantal; Collet, Andre. Unite Mixte Rech., Ec. Norm. Super. Lyon, Lyon, Fr. Supramol. Chem. (1992), 1(1), 31-45. CODEN: SCHEER ISSN: 1061-0278. Journal written in English. CAN 118:147280 AN 1993:147280 CAPLUS
Abstract
Vanillin and isovanillin were converted via a Newman-Kwart rearrangement to thiovanillin and isothiovanillin, which on S-methylation and subsequent redn. of the aldehyde function gave 3-methoxy-4-methylthio- (I) and 4-methoxy-3-methylthiobenzyl alc. (II), resp.
If someone can get this ref or know if the Newman-Kwart rearrangement is readily applicable it would be cool to share this info with us.
aloha P
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