Assignment of cis–trans Configuration to 1,2-Dialkylcyclohexanes
✍ Scribed by NATALIS, P.
- Book ID
- 109622498
- Publisher
- Nature Publishing Group
- Year
- 1962
- Tongue
- English
- Weight
- 108 KB
- Volume
- 195
- Category
- Article
- ISSN
- 0028-0836
- DOI
- 10.1038/195380a0
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📜 SIMILAR VOLUMES
## Abstract On irradiation (__λ__=350 nm), 1,2‐naphthoquinone (=naphthalene‐1,2‐dione) monoacetals **1** are converted quantitatively to mixtures of the __cis‐trans‐cis__‐photocyclodimers **2** and **3**. Careful hydrolysis of each of the (parent) pentacyclic diacetals **2a** and **3a** affords the
2 (92%), 3 (5%) 4 (93^/0), 5 (5%) 8 (899;8), 9 (6%) 10 (90%), 11 (5%) 14 (88%), 15 (6%) 16 (90%), 17 (5%) 20 (86%), 21 (9%) 22 (84%), 23 (9%) Surprisingly, under analogous conditions, the CI -u-mannopyranose 7') also yielded the 1,2-cis-configurated dimethyl and diethyl phosphonates 8 (89%) and 10 (