13C labeled benzo[a]pyrenes and derivatives. 2. The synthesis of benzo[a]pyrene-6-13C
✍ Scribed by J. Ernest Simpson; Guido H. Daub; David L. Vanderjagt
- Publisher
- John Wiley and Sons
- Year
- 1980
- Tongue
- French
- Weight
- 240 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0022-2135
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
The synthesis of benzo[a]pyrene‐6‐^13^C is described. Perinaphthane was converted to 6‐benzoyl‐carbonyl‐^13^C‐perinaphthane which was cyclized to 2,3‐dihydrobenzo[a]pyren‐6(1H)‐one‐6‐^13^C. Subsequent reduction of the ketone followed by dehydration and dehydrogenation gave benzo[a]pyrene‐6‐^13^C in 29% overall yield.
📜 SIMILAR VOLUMES
## Abstract Sodium formate‐^13^C, prepared by hydrolysis of isopropyl formate, was allowed to react with N‐methylaniline hydrochloride to prepare the formylating agent N‐methylformanilide‐1‐^13^C. Formylation of benzo(a)pyrene with N‐methylformanilide‐1‐^13^C gave the 6‐^13^CHO derivative which was
A t e n step synthesls o f b e n ~o [ a ] p y r e n e -l -~3 C , -2-l3C, o r 3-13C from 2,3,7, llb-tetrahydrobenr[d,e]anthracen-3(1H)-one t s descrlbed t n whtch t h e l n l t l a l step I n v o l v e s t h e condensatlon o f t h l s ketone w l t h t h e l l t h l u m enolate o f e t h y l acetate.
## Abstract 6‐Lithiobenzo[__a__]pyrene was carbonated to produce benzo[__a__]pyrene‐6‐carboxylic‐^14^C acid, which was in turn used in the preparation of several derivatives. Methylation to the ester was followed by LiAlH~4~ reduction to 6‐hydroxymethyl‐^14^C‐benzo[__a__]pyrene. An efficient oxidat