58239-40-0

Upstream product

• 117679-03-5 (anti)-Tricyclo<4.3.1.0^1,6>dec-3-en-10-amine 
• 117679-04-6 (syn)-Tricyclo<4.3.1.0^1,6>dec-3-en-10-amine 

Downstream Products

• 42788-28-3 3,5-Dinitro-benzoic acid 2,3-dihydro-1H-3a,7a-methano-inden-8-ylmethyl ester 
• 42868-30-4 3,5-Dinitro-benzoic acid hexahydro-3a,7a-methano-inden-8-ylmethyl ester 
• 54786-33-3 3,5-Dinitro-benzoic acid 2,3,4,5-tetrahydro-1H-3a,7a-methano-inden-8-ylmethyl ester 
• 42788-27-2 3,5-Dinitro-benzoic acid 2,3,4,7-tetrahydro-1H-3a,7a-methano-inden-8-ylmethyl ester 

Relevant academic research and scientific papers

Deamination Reactions, 52. - Cyclopropanediazonium Ions Derived form Propellanes

Tricyclo1,6>dec-3-en-10-amines (16, 17) and their saturated analogs (18, 19) were prepared by a multistep sequence, starting from ethyl 2-oxo-cyclopentanecarboxylate (8).The intermediate tricyclo1,6>dec-3-ene-10-carboxylic acids (14) were separated and configurationally assigned by iodolactonization of the syn isomer.Nitrous acid deaminations of the amines 16 - 19 were preformed in aqueous lithium bromide solutions.Thus, the intervening carbocations were trapped to give stable tricyclic bromides 23 - 26 as the major products.Predominant retention of the configuration was observed with all substrates although the syn-amine 17 deviated significantly from its anti isomer 16 and from the higher homologs.Charge delocalization in the tricyclic cation 31 appears to be enhanced relative to the bicyclohex-3-yl cation (3). - Keywords: Diazonium Ions/ Nucleophilic displacement/ Propellanes/ Tricyclo1,6>dec-10-yl derivatives