An amino-3,4-dihydro-2H-1,3,5-thiadiazin-2-one synthesisviaa novel carbamoyl chloride

Author:

Chupp John P.

Publisher

Wiley

Subject

Organic Chemistry

Reference12 articles.

1. Ring closures from eneearbamoyl azides. Syntheses of tetrahydro-3-indazolinones and 4-imidazolin-2-ones

2. Ring closures from enecarbamoyl thiocyanates. Syntheses of 5,6,7,8-tetrahydro-4-thio-2,4(lH,3H)-quinazolinediones and related compounds

3. Reaction of certain electrophiles with some imines derived from cyclohexanone and isobutyraldehyde

4. A clue to its unusual stability may be revealed by the very large (ca. 10 Hz) coupling constant for the vicinal protons. The large J value observed would, from the Karplus equation, arise from a fairly rigid, skeletal structure with the 1,2-protons positioned trans (or 180°) to each other. This conformation, with the chlorine cis, rather than trans to the β-hydrogen would inhibit dehydrohalogenation via an energetically less favorable cis elimination.

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