Synthesis of 2H-1-Benzthiocin: a Precursor for the Generation of the "4n+2" Pi-electron 1-Benzthiocinide Anion.

<p>2-Mercaptobenzenemethaol <strong>14</strong> was prepared by LAH reduction of 2-mercaptobenzoic acid (thiosalicylic acid) in 95% yield. Oxidation of it with PCC afforded 2,2'-dithiobenzaldehyde <strong>15</strong> in 52% yield. A selective reduction of disulfide <strong>15</strong> to 2-mercaptobvenzaldehyde <strong>16</strong> was achieved using triphenylphosphene in MeOH-H₂O-DMF solvent mixture. The reaction of <strong>16</strong> with KOH in the presence of 18-crown-6 followed by addition of 1,4-dibromobutane resulted in 4-(o-formylphenthio)butyl bromide <strong>17</strong> which was converted to triphenylphosphonium bromide salt <strong>18</strong> in 75% yield. Wittig cyclization of <strong>18</strong> with K-t-BuO afforded 3,4-dihydro-2H-1-benzthiocin <strong>19</strong> in 71% yield. In an attempt to prepare 2H-1-benzthiocin <strong>13</strong> via dehydrobromination of bromo compound <strong>20</strong>, compound <strong>19</strong> was treated with NBS in the presence of catalytic amount of benzoyl peroxide. However, from the complex reaction mixture, only the dibromo compound <strong>21</strong> was isolated and identified.</p>

Name thesis:degree_name

MS (Master of Science)

Level thesis:degree_level

Thesis - restricted

Discipline thesis:degree_discipline

Chemistry

Year dc:date.issued

2001

Author dc:creator

• Tang, Mingnam

• Oganic synthesis of 1-Benzthiocin
• Chemistry
• Physical Sciences and Mathematics

Statement dc:rights

• Copyright by the authors.

Repository record dc:identifier

https://dc.etsu.edu/etd/50

OAI identifier oai:identifier

oai:dc.etsu.edu:etd-1100