1-propanamine to cyclopropane?

I was solving some questions on amines when I happened to see the below question:



> 
> propan-1-amine + ($\ce{NaNO2 + HCl}$)= a mixture of products 
>  (originally, the mixture in brackets on the reactant side was just
>  written as $\ce{HNO2}$)
> 
> 
> The mixture contains:
> 
> 
> a. 1-Propanol
> 
> 
> b. 2-Propanol
> 
> 
> c. Cyclopropane
> 
> 
> d. All of these
> 
> 
> 


The answer happened to be "d. All of these". I could understand the formation of 1-propanol and 2-propanol but not cyclopropane. The answer given in the textbook wasn't clear and I couldn't understand. It said that the carbocation intermediate had something to do with it which I couldn't follow.


Can someone explain what is behind all this?




* Diazotisation of primary amines gives the diazonium salt which decomposes to the primary cation and $\ce{N2}$. From this, in aq. $\ce{HCl}$, you directly get the primary alcohol, primary chloride and primary nitro by immediate trapping of the primary cation by ions in solution and the terminal alkene by 1,2 elimination.
* A cation shift to give the secondary cation also occurs to give secondary alcohol and secondary chloride.
* The cyclopropane arises from a 1,3-elimination of the primary cation.


[![enter image description here](https://i.stack.imgur.com/aJsio.png)](https://i.stack.imgur.com/aJsio.png)


[![enter image description here](https://i.stack.imgur.com/qlaDX.png)](https://i.stack.imgur.com/qlaDX.png)


[![enter image description here](https://i.stack.imgur.com/PYuOE.png)](https://i.stack.imgur.com/PYuOE.png)


pics from reference 1 


**References**


1. [Amines with Nitrous Acid - chem.libretexts.org](https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/23%3A_Organonitrogen_Compounds_I-_Amines/23.10%3A_Amines_with_Nitrous_Acid)
2. *Nitrosation, diazotisation, and deamination* by J. H. Ridd Q. Rev. Chem. Soc., **1961**, 15, 418-441 DOI: <https://doi.org/10.1039/QR9611500418>


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